利用串联反应构建几类含氮杂环化合物
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摘要
1,2-二氢异喹啉、喹啉、吲哚等杂环是许多天然产物的核心结构单元,广泛存在于天然产物和药物中,通常具有广泛的生物活性。由于该类结构单元不仅是众多天然分子及合成分子的亚结构单元,也是生物碱全合成的重要中间体,化学工作者正努力开发基于该类骨架单元的新型结构及其全新的合成方法。尽管已经有多种方法可以构建该类化合物,但是发展新的方法,能够从简单易得的原料出发,合成多取代的该类杂环化合物仍然具有重要意义。本论文主要研究了基于多组分串联反应合成1,2-二氢异喹啉、喹啉、吲哚等含氮杂环化合物的方法。
1.研究了CuI催化的邻炔基苯甲醛、胺、亚磷酸二乙酯三组分串联环化反应,采用一锅法方便有效合成2,3-二取代的1,2-二氢异喹啉基膦酸酯,反应可能经过异喹啉盐中间体的过程。还发现了一种基于AgOTf催化的邻炔基苯甲醛、胺、NaBH_4三组分,一锅法有效合成1,2-二氢异喹啉衍生物的方法。与此同时,我们还探讨了将金属和有机小分子催化剂相结合的双活化策略应用于多组分串联环化反应,邻炔基苯甲醛、胺、酮的三组分于一锅中合成1,2-二氢异喹啉衍生物。而且,我们还发现2-炔基苯甲醛肟使用AgOTf和Yb(OTf)_3共催化剂可以实现串联亲电环化和[3+3]环加成反应,合成1,2,3,11b-四氢-[1,2]嗪并[3,2-a]异喹啉骨架化合物。
2.发现2-炔基-α-氨基-苄基膦酸酯可在过渡金属(Pd/Ag)调控下选择性合成2,3-二取代的异吲哚基膦酸酯和2,3-二取代的1,2-二氢异喹啉基膦酸酯化合物。同时还发现2-炔基-α-氨基-苄基膦酸酯可在Pd(0)催化下发生分子内串联5-exo-环化/[1,5]-H迁移反应,再串联芳基碘的交叉偶联反应,以高产率得到多官能团化的异吲哚基膦酸酯衍生物。
3.使用亲电环化/交叉偶联的方法,从2-炔基苯甲醛肟和I_2、Br_2、NBS、NIS、ICl等亲电试剂出发,在非常温和的条件下以非常简便、高效的方法合成了一系列高官能团化的异喹啉-N-氧化物。同时我们从2-炔基苯甲醛肟和DMAD以及溴出发,实现了一锅法串联亲电环化-[3+2]环加成-重排反应,高效生成基于异喹啉骨架叶立德化合物,再经Suzuki-Miyaura交叉偶联反应将上述叶立德产物进一步引入多样性。而且,我们还发展了一种在温和条件下亲电试剂(I_2/Br_2/ICl)与2-炔基苯腙类化合物之间发生亲电环化生成具有异喹啉骨架的新方法。
4.发现2-炔基苯胺与异硫氰酸酯在AgOTf催化作用下发生串联加成-环化反应,高效合成2,4-二氢-1H-苯并[d]-[1,3]噻嗪亚胺衍生物。同时我们还实现了CuI催化的2-碘苯胺与异硫氰酸酯之间的串联加成-环化反应,方便地得到2-氨基苯并噻唑类化合物。
It is well-known that the 1,2-dihydroisoquinoline,isoindole and isoquinoline rings are the most ubiquitous heterocyclic motifs and are found in many natural products and pharmaceuticals that exhibit remarkable biological activities.Significant effort continues to be given to the development of new 1,2- dihydroisoquinoline- or isoindole- or isoquinoline-based structures and new methods for their construction, due to their importance as substructures in a broad range of natural and designed products as well as synthetic intermediates in total synthesis of natural alkaloids. Although a number of protocols have been established to construct these compounds, the development of novel methodologies that allows the facile assmbly of substituded heterocycles from readily available starting materials remains an important objective. This dissertation is mainly foused on the tandem reactions for synthesis of 1, 2-dihydroisoquinoline,isoindole and isoquinoline rings.
Firstly,we described copper(Ⅰ) iodide catalyzed three-component reactions of 2-alkynyl benzaldehydes,amines,and diethyl phosphite,leading to the 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonates.Isoquinolinium intermediate may be involved in the reaction process.We also described AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldehydes,amines,and sodium borohydride under mild conditions,which provide a facile and efficient protocol to facilitate the concise synthesis of 1,2-dihydroisoquinoline derivatives.Another novel and highly effective one-pot combination of AgOTf and proline catalysis for the synthesis of 1,2-dihydroisoquinoline derivatives via multicomponent reactions of 2-alkynylbenzaldehydes,amines,and ketones was disclosed as well.In addition,a combination of AgOTf and Yb(OTf)_3 as catalyst was demonstrated highly effective in the tandem cyclization-[3+3]cycloaddition reaction of 2-alkynylbenzaldoxime with dimethyl cyclopropane-1,1-dicarboxylate,which generated the tetrahydro-1,2-oxazine-fused 1,2-dihydroisoquinolines in good yield.
Secondly,we investigaeted the palladium(Ⅱ)-or silver(Ⅰ)-catalyzed reactions ofα-amino(2-alkynylphenyl)methylphosphonate.We found that this metal-tuned reaction provide a novel and efficient route to 2,3-disubstituted-2H-isoindol-1-ylphosphonate or 2,3-disubstituted- 1,2-dihydroisoquinolin-1-ylphosphonate.Moveover,we realized the efficient synthesis of isoindol-1-ylphosphonate derivatives via Pd(0)-catalyzed reaction ofα-amino(2-alkynylphenyl) methylphosphonate with aryl iodide.
Next,we disclosed a highly efficient and general method for the generation of functionalized isoquinoline N-oxides via sequential electrophilic cyclization/cross-coupling reactions of 2-alkynylbenzaldoximes with I_2,Br_2,NBS, NIS or ICI under mild conditions.Meanwhile,an unexpected generation of isoquinoline-based azomethine ylides starting from 2-alkynylbenzaldoximes,DMAD, and bromine via tandem electrophilic cyclization-[3+2]cycloaddition-rearrangement reactions was discovered.These products could be further elaborated by Suzuki-Miyaura couplings to introduce more diversity.We also described a highly efficient electrophilic cyclization of N'-(2-alkynylbenzylidene)-hydrazide with I_2,Br_2, or ICI in dichloromethane at room temperature.This reaction proceeds smoothly under extremely mild conditions,which provides a useful method for the synthesis of functionalized isoquinolinium-2-yl amides.
Finally,the tandem addition-cyclization reactions of 2-alkynylbenzenamines with isothiocyanates catalyzed by silver triflate were investigated,and the desired 2,4-dihydro-1Hbenzo[d][1,3]thiazines was obtained in good yield.Meanwhile,the construction of 2-aminobenzothiazole was realized in copper(Ⅰ)-catalyzed tandem reaction of 2-iodobenzenamine with isothiocyanate under mild conditions.
1.研究了CuI催化的邻炔基苯甲醛、胺、亚磷酸二乙酯三组分串联环化反应,采用一锅法方便有效合成2,3-二取代的1,2-二氢异喹啉基膦酸酯,反应可能经过异喹啉盐中间体的过程。还发现了一种基于AgOTf催化的邻炔基苯甲醛、胺、NaBH_4三组分,一锅法有效合成1,2-二氢异喹啉衍生物的方法。与此同时,我们还探讨了将金属和有机小分子催化剂相结合的双活化策略应用于多组分串联环化反应,邻炔基苯甲醛、胺、酮的三组分于一锅中合成1,2-二氢异喹啉衍生物。而且,我们还发现2-炔基苯甲醛肟使用AgOTf和Yb(OTf)_3共催化剂可以实现串联亲电环化和[3+3]环加成反应,合成1,2,3,11b-四氢-[1,2]嗪并[3,2-a]异喹啉骨架化合物。
2.发现2-炔基-α-氨基-苄基膦酸酯可在过渡金属(Pd/Ag)调控下选择性合成2,3-二取代的异吲哚基膦酸酯和2,3-二取代的1,2-二氢异喹啉基膦酸酯化合物。同时还发现2-炔基-α-氨基-苄基膦酸酯可在Pd(0)催化下发生分子内串联5-exo-环化/[1,5]-H迁移反应,再串联芳基碘的交叉偶联反应,以高产率得到多官能团化的异吲哚基膦酸酯衍生物。
3.使用亲电环化/交叉偶联的方法,从2-炔基苯甲醛肟和I_2、Br_2、NBS、NIS、ICl等亲电试剂出发,在非常温和的条件下以非常简便、高效的方法合成了一系列高官能团化的异喹啉-N-氧化物。同时我们从2-炔基苯甲醛肟和DMAD以及溴出发,实现了一锅法串联亲电环化-[3+2]环加成-重排反应,高效生成基于异喹啉骨架叶立德化合物,再经Suzuki-Miyaura交叉偶联反应将上述叶立德产物进一步引入多样性。而且,我们还发展了一种在温和条件下亲电试剂(I_2/Br_2/ICl)与2-炔基苯腙类化合物之间发生亲电环化生成具有异喹啉骨架的新方法。
4.发现2-炔基苯胺与异硫氰酸酯在AgOTf催化作用下发生串联加成-环化反应,高效合成2,4-二氢-1H-苯并[d]-[1,3]噻嗪亚胺衍生物。同时我们还实现了CuI催化的2-碘苯胺与异硫氰酸酯之间的串联加成-环化反应,方便地得到2-氨基苯并噻唑类化合物。
It is well-known that the 1,2-dihydroisoquinoline,isoindole and isoquinoline rings are the most ubiquitous heterocyclic motifs and are found in many natural products and pharmaceuticals that exhibit remarkable biological activities.Significant effort continues to be given to the development of new 1,2- dihydroisoquinoline- or isoindole- or isoquinoline-based structures and new methods for their construction, due to their importance as substructures in a broad range of natural and designed products as well as synthetic intermediates in total synthesis of natural alkaloids. Although a number of protocols have been established to construct these compounds, the development of novel methodologies that allows the facile assmbly of substituded heterocycles from readily available starting materials remains an important objective. This dissertation is mainly foused on the tandem reactions for synthesis of 1, 2-dihydroisoquinoline,isoindole and isoquinoline rings.
Firstly,we described copper(Ⅰ) iodide catalyzed three-component reactions of 2-alkynyl benzaldehydes,amines,and diethyl phosphite,leading to the 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonates.Isoquinolinium intermediate may be involved in the reaction process.We also described AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldehydes,amines,and sodium borohydride under mild conditions,which provide a facile and efficient protocol to facilitate the concise synthesis of 1,2-dihydroisoquinoline derivatives.Another novel and highly effective one-pot combination of AgOTf and proline catalysis for the synthesis of 1,2-dihydroisoquinoline derivatives via multicomponent reactions of 2-alkynylbenzaldehydes,amines,and ketones was disclosed as well.In addition,a combination of AgOTf and Yb(OTf)_3 as catalyst was demonstrated highly effective in the tandem cyclization-[3+3]cycloaddition reaction of 2-alkynylbenzaldoxime with dimethyl cyclopropane-1,1-dicarboxylate,which generated the tetrahydro-1,2-oxazine-fused 1,2-dihydroisoquinolines in good yield.
Secondly,we investigaeted the palladium(Ⅱ)-or silver(Ⅰ)-catalyzed reactions ofα-amino(2-alkynylphenyl)methylphosphonate.We found that this metal-tuned reaction provide a novel and efficient route to 2,3-disubstituted-2H-isoindol-1-ylphosphonate or 2,3-disubstituted- 1,2-dihydroisoquinolin-1-ylphosphonate.Moveover,we realized the efficient synthesis of isoindol-1-ylphosphonate derivatives via Pd(0)-catalyzed reaction ofα-amino(2-alkynylphenyl) methylphosphonate with aryl iodide.
Next,we disclosed a highly efficient and general method for the generation of functionalized isoquinoline N-oxides via sequential electrophilic cyclization/cross-coupling reactions of 2-alkynylbenzaldoximes with I_2,Br_2,NBS, NIS or ICI under mild conditions.Meanwhile,an unexpected generation of isoquinoline-based azomethine ylides starting from 2-alkynylbenzaldoximes,DMAD, and bromine via tandem electrophilic cyclization-[3+2]cycloaddition-rearrangement reactions was discovered.These products could be further elaborated by Suzuki-Miyaura couplings to introduce more diversity.We also described a highly efficient electrophilic cyclization of N'-(2-alkynylbenzylidene)-hydrazide with I_2,Br_2, or ICI in dichloromethane at room temperature.This reaction proceeds smoothly under extremely mild conditions,which provides a useful method for the synthesis of functionalized isoquinolinium-2-yl amides.
Finally,the tandem addition-cyclization reactions of 2-alkynylbenzenamines with isothiocyanates catalyzed by silver triflate were investigated,and the desired 2,4-dihydro-1Hbenzo[d][1,3]thiazines was obtained in good yield.Meanwhile,the construction of 2-aminobenzothiazole was realized in copper(Ⅰ)-catalyzed tandem reaction of 2-iodobenzenamine with isothiocyanate under mild conditions.
引文
[1](a) Hinterding,K.;Alonso-Diaz,D.;Waldmann,H.Angew.Chem.Int.Ed.,1998,37:688-749;
(b) Hung,D.T.;Jamison,T.F.;Schreiber,S.L.Chem.Biol.,1996,3,623-639.
[2]Fergus,S.;Bender,A.;Spring,D.R.Curr.Opin.Chem.Biol.,2005,9,304-309.
[3](a) Nicolaou,K.C.;Yang,Z.;Liu,J.-J.;Ueno,H.;Nantermet,P.G.;Guy,R.K.Nature 1994,367,630-634;
(b) Nicolaou,K.C.;Nantermet,P.G.;Ueno,H.;Guy,R.K.;Couladouros,E.A.;Sorensen,E.J.J.Am.Chem.Soc.1995,117,624-633;
(c)Nicolaou,K.C.;Liu,J.-J.;Yang,Z.;Ueno,H.;Sorensen,E.J.;Claiborne,C.F.;Guy,R.K.;Hwang,C.-K.;Nakada,M.;Nantermet,P.G.J.Am.Chem.Soc.1995,117,633-644;
(d) Nicolaou,K.C.;Yang,Z.;Liu,J.-J.;Nantermet,P.G.;Claiborne,C.F.;Renaud,J.;Guy,R.K.;Shibayama,K.;J.Am.Chem.Soc.1995,117,645-652;
(d)Nicolaou,K.C.;Ueno,H.;Liu,J.-J.;Nantermet,P.G.;Yang,Z.;Renaud,J.;Pauivannan,K.;Chadha,R.J.Am.Chem.Soc.1995,117,653-659.
[4]Tempest,P.A.;Armstrong,R.W.J.Am.Chem.Soc.1997,119,7607-7608.
[5]Marx,M.A.;Griliot,A-L;Louer,C.T.;Beaver,K.A.;Bartlett,P.A.J.Am.Chem.Soc.1997,119,6153-6167.
[6]Reayi,A.;Arya,P.Curr.Opin.Chem.Biol.2005,9(3),240-247.
[7]Schreiber,S.L.Science 2000,287,1964-1969.
[8](a) Shang,S.Y.;Tan,D.S.;Curt.Opin.Chem.Biol.2005,9(3),248-258;
(b)刘钢(Liu,G);李裕林(Li,Y.L.);南发俊(Nan,F.J.),化学进展(Progress in Chemistry),2006,18(6),734-742.
[9]Pelish,H.E.;Westwood,N.J.;Feng,Y;Shair,M.D.et al.J.Am.Chem.Soc.2001,123,6740-6741.
[10]Lo,M.M.C.;Neumann,C.S.;Nagayama,S.;Perlstein,E.O.;Schreiber,S.L.J.Am.Chem.Soc.2004,126,16077-16086.
[11]Ding,K.;Lu,Y.P.;Nikolovska-Coleska,Z.;Wang,S.M.et al.J.Am.Chem.Soc.2005,127,10130-10131.
[12](a) Nicolaou,K.C.;Pfefferkorn,J.A.;Roecker,A.J.;Cao,G.Q.;Barluenga,S.;Mitchell,H.J.J.Am.Chem.Soc.2000,122,9939-9953;
(b) Nicolaou,K.C.;Pfefferkorn,J.A.;Mitchell,H.J.;Roecker,A.J.;Barluenga,S.;Cao,G.Q.;Affleck,R.L.;Lillig,J.E.J.Am.Chem.Soc.2000,122,9954-9967;
(c)Nicolaou,K.C.;Pfefferkorn,J.A.;Barluenga,S.;Mitchell,H.J.;Roecker,A.J;Cao,G.Q.J.Am.Chem.Soc.,2000,122,9968-9976.
[13](a) Nicolaou,K.C.;Pfefferkorn,J.A.;Schuler,F.;Roecker,A.J.;Cao,G.Q.;Casida,J.E.Chem.Biol.2000,7,979-992.
[14]Nicolaou,K.C.;Roecker,A.J.;Barluenga,S.;Pfefferkorn,J.A.;Cao,G.Q.Chembiochem,2001,2,460-465.
[15]Nicolaou,K.C.;Evans,R.M;Roecker,A.J.;Hughes,R.;Downes,M.;Pfefferkorn,J.A.Org.Biomol.Chem.2003,/,908-920.
[16]Michael,J.P.Nat.Prod.Rep.2004,21,650-668.
[17](a) Arya,P.;Durieux,P.;Chen,Z.X.;Joseph,R.;Leek,D.M.J.Comb.Chem.2004,6,54-64;(b) Arya,P.Couve2Bonnaire,S.;Durieux,P.et al.J.Comb.Chem.2004,6,735-745;(c) Khadem,S.;Joseph,R.;Rastegar,M.;Oudatchin,K.A.;Arya,P.J.Comb.Chem.2004,6,724-734.
[18]Slee,D.H.;Bhat,A.S.;Nguyen,T.N.;Kish,M.;Lundeen,K.;Newman,M.J.;McConnell,S.J.J.Med.Chem.2003,46,1120-1122.
[19]Barun,O.;Sommer,S.;Waldmann,H.Angew.Chem.Int.Ed.2004,43,3195-3199.
[20](a)Sternson,S.M.;Louca,J.B.;Wong,J.C;Schreiber,S.L.J.Am.Chem.Soc.2001,123,1740-1747;(b) Wong,J.C;Sternson,S.M.;Louca,J.B.;Hong,R.;Schreiber,S.L.Chem.Biol.2004,11,1279-1291.
[21]Kuruvilla,F.G.;Shamji,A.F.;Sternson,S.M.;Hergenrother,P.J.;Schreiber,S.L.Nature,2002,416,653-657.
[22]Haggarty,S.J.;Koeller,K.M.;Wong,J.C;Grozinger,CM.;Schreiber,S.L.Proc.Natl.Acad.Sc.USA,2003,100,4389-4394.
[23]Taylor,S.J.;Taylor,A.M.;Schreiber,S.L.Angew.Chem.Int.Ed.2004,43,1681-1685.
[24]Weber,L.Curr.Med.Chem.2002,9(23),2085-2093.
[25]Povarov,L.S.;Mikhailov,B.M.;Izvestiya Akademii Nauk SSSR,Seriya Khimicheskaya,1963,955-956.
[26]Nicolaou,K.C.;Cao,G.Q.;Pfefferkorn,J.A.;Angew.Chem.Int.Ed.2000,39,739-743.
[27]Andreana,P.R.;Liu,C.C.;Schreiber,S.L.Org.Lett.2004,6,4231-4233.
[28]Tietze,L.F.;Rackelmann,N.;Sekar,G.Angew.Chem.In.Ed.2003,42,4254-4257.
[29]Young,I.S.;Kerr,M.A.Angew.Chem.Int.Ed.2003,42,3023-3026.
[30]Arya,P.;Joseph,R.;Gan,Z.G.;Rakic,B.Chemistry & Biology 2005,12,163 -180.
[31]Clardy,J.;Walsh,C.Nature,2004,432,829-837.
[32]Ho,T.Tactics of Organic Synthesis.Wiley,1994.
[33]Denmark,S.E.;Thorarensen,A.Chem Rev,1996,96(1),137.
[34]Kataoka,T.;Kinoshita,H.;Kinoshita,S.;Tatsunori,I.Tetrahedron Lett.2002,43,7039.
[35]Wang,W.;Li,H.;Wang,J.;Zu,L.S.J.Am.Chem.Soc.,2006,128(32),10354-10355.
[36]Stelmakh,A.;Stellfeld,T.;Kalesse,M.;Org.Lett.2006,8(16),3485-3488.
[37]Bogdanowicz-Szwed,K.;Gil,R.Monatsh.Chem.2004,135,1415.
[38]Ballini,R.;Buciano,L.;Fiorini,D.;Giarlo,G.Chem.Commun.2005,(20),2633.
[39]Ferna,M.;Alonso,R.Org.Lett.2005,7,11.
[40]Chen,Y.J.;Chen,C.M.;Lin,W.Y.Tetrahedron Lett,1993,34(18),2961.
[41]RamaRao,V.V.V.N.S.;Venkat-Reddy,G.;Maitraie,D.;Ravikanth,S.;Yadla,R.;Narsaiah,B.;Shanthan-Rao,P.Tetrahedron 2004,60,12231.
[42]Ram,V.J.;Goel,A.;Sarkhe,S.;Maulik,P.R.Bioorg.Med.Chem.2002,10,1275.
[43]Ewold,W.D.;Panella,L.;Pinho,P.;Maulik P.R.Tetrahedron 2004,60,9687.
[44]Glushkov,V.A.;Shurov,S.N.;Maioroval,O.A.;Postanogoval,G.A.Chem.Heterocycl.Compd.2001,37,444.
[45]Lin,Y.-L.;Kuo,H.-S.;Wang,Y.-W.;Huang,S.-T.Tetrahedron 2003,59,1277.
[46]Wang,J.-W.;Jia,J.;Hou,D.-J.;Li,H.-M.;Yin,J.Chin.J.Org.Chem.2003,23,173(in Chinese).(
王建武,贾炯,候殿杰,李红梅,尹军,有机化学,2003,23,173.)
[47]Mc-Dermott,P.J.;Stockman,R.A.Org.Lett.2005,7,27.
[48]De-Boeck,B.;Harrington-Frost,N.M.;Pattenden,G.Org.Biomol.Chem.2005,3,340.
[49]Handa,S.;Pattenden,G.Chem Comm un,19989,3,311.
[50]Majumdar,K.C.;Samanta,S.K.Tetrahedron Lett.2002,43,2119.
[51]Alcaide,B.;Almendros,P.;Aragoncillo,C.;Redondo,M.C.Eur.J.Org.Chem.2005,3,98.
[1]For selected examples,see:(a) Bentley,K.W.The Isoquinoline Alkaloids;Harwood Academic:Australia,1998;Vol 1.(b) Trotter,B.W.;Nanda,K.K.;Kett,N.R.;Regan,C.P.;Lynch,J.J.;Stump,G.L.;Kiss,L.;Wang,J.;Spencer,R.H.;Kane,S.A.;White,R.B.;Zhang,R.;Anderson,K.D.;Liverton,N.J.;Mclntyre,C.J.;Beshore,D.C;Hartman,G.D.;Dinsmore,C.J.J.Med.Chem.2006,49,6954.(c) Ramesh,P.;Reddy,N.S.;Venkateswarlu,Y.J.Nat.Prod 1999,62,780.(d) Oi,S.;Ikedou,K.;Takeuchi,K.;Ogino,M.;Banno,Y.;Tawada,H.;Yamane,T.PCT Int.Appl.2002,600 pp (WO 2002062764 Al).
[2]For selected examples,see:(a) Scott,J.D.;Williams,R.M.Chem.Rev.2002,102,1669.(b) Chan,C;Heid,R.;Zheng,S.;Guo,J.;Zhou,B.;Furuuchi,T.;Danishefsky,S.J.J.Am.Chem.Soc.2005,127,4596.(c) Magnus,P.;Matthews,K.S.J.Am.Chem.Soc.2005,127,12476.(d) Zheng,S.;Chan,C;Furuuchi,T.;Wright,B.J.D.;Zhou,B.;Guo,J.;Danishefsky,S.D.Angew.Chem.,Int.Ed.2006,45,1754.(e) Vincent,G.;Williams,R.M.Angew.Chem.,Int.Ed.2007,46,1517.
[3](a) Obika,S.;Kono,H.;Yasui,Y.;Yanada,R.;Takemoto,Y.J.Org.Chem.2007,72,4462.(b) Asao,N.;Yudha S.,S.;Nogami,T.;Yamamoto,Y.Angew.Chem.Int.Ed.2005,44,5526.(c) Yanada,R.;Obika,S.;Kono,H.;Takemoto,Y.Angew.Chem.Int.Ed.2006,45,3822.(d) Asao,N.;Iso,K.;Yudha S.,S.Org.Lett.2006,8,4149.(e) Mori,S.;Uerdingen,M.;Krause,N.;Morokuma,K.Angew.Chem.Int.Ed.2005,44,4715.(f) Asao,N.;Chan,C.S.;Takahashi,K.;Yamamoto,Y.Tetrahedron 2005,61,11322.(g) Ohtaka,M.;Nakamura,H.;Yamamoto,Y.Tetrahedron Lett.2004,45,7339.(h) Witulski,B.;Alayrac,C;Tevzadze-Saeftel,L.Angew.Chem.Int.Ed.2003,42,4257.(i) Yavari,I.;Ghazanfarpour-Darjani,M.;Sabbaghan,M.;Hossaini,Z.Tetrahedron Lett.2007,48,3749.(j) Shaabani,A.;Soleimani,E.;Khavasi,H.R.Tetrahedron Lett.2007,48,4743.(k) Wang,G.-W.;Li,J.-X.Org.Biomol.Chem.2006,4,4063.(1) Diaz,J.L.;Miguel,M.;Lavilla,R.J.Org.Chem.2004,69,3550.
[4](a) Huang,Q.;Larock,R.C.J.Org.Chem.2003,68,980.(b) Dai,G.;Larock,R.C.J.Org.Chem.2003,68,920.(c) Dai,G.;Larock,R.C.J.Org.Chem.2002,67,7042.(d) Huang,Q.;Hunter,J.A.;Larock,R.C.J.Org.Chem.2002,67,3437.(e)Roesch,K.R.;Larock,R.C.J.Org.Chem.2002,67,86.(f) Roesch,K.R.;Zhang,H.;Larock,R.C.J.Org.Chem.2001,66,8042.(g) Roesch,K.R.;Larock,R.C.Org.Lett.1999,1,553.
[5]Croisy-Delcey,M.;Croisy,A.;Carrez,D.;Huel,C;Chiaroni,A.;Ducrot,P.; Bisagni,E.;Jin,L.;Leclercq,G.Bioorg.Med.Chem.2000,8,2629.
[6]Whaley,W.M.;Govindachari,T.R.In Organic Reactions;Adams,R.,Ed.;Wiley:New York,1951;Vol.6,pp 151-190.
[7]Gensler,W.J.In Organic Reactions;Adams,R.,Ed.;Wiley:NewYork,1951;Vol.6,pp 191-206.
[8](a) Maassarani,F.;Pfeffer,M.;Le Borgne,G.J.Chem.Soc,Chem.Commun.1987,565.(b) Wu.G.;Geib.S.J.;Rheingold,A.L.;Heck,R.F.J.Org.Chem.1988,53,3288.(c) Girling,I.R.;Widdowson,D.A.Tetrahedron Lett.1982,23,4281.(d)Roesch,K.R.;Larock,R.C.J.Org.Chem.1998,63,5306.
[9]Dai,G.X.;Larock,R.C.,Org.Lett.,2001,3,4035;Dai,G.X.;Larock,R.C.,J.Org.Chem.2003,68,920-928
[10](a) Arcadi,A.;Cacchi,S.;Fabrizi,G.;Moro,L.Eur.J.Org.Chem.1999,64,1137.(b) Cacchi,S.;Fabrizi,G.;Pace,P.;Marinelli,F.Synlett 1999,5,620.(c)Arcadi,A.;Cacchi,S.;Carnicelli,V.;Marinelli,F.Tetrahedron 1994,50,437.
[11]Arcadi,A.;Cacchi,S.;Rosario,M.D.;Fabrizi,G.;Marinelli,F.J.Org.Chem.1996,61,9280.
[12]Dai,G.X.;Larock,R.C.,Org.Lett.,2002,4,193.
[13]Huang,Q.H.;Hunter,J.A.;Larock,R.C.Org.Lett.2001,3,2973.
[14]Su,S.;Porco,Jr.J.A.J.Am.Chem.Soc,2007,129,7744.
[15]Nakamura,H.;Saito,H.;Nanjo,M.Tetrahedron Lett.2008,49,2697.
[16](a) Engel,R.Handbook of Organophosphorus Chemistry;Marcel Dekker,Inc.:New York,1992.(b) Kafarski,P.;Lejczak,B.Phosphorus Sulfur Silicon Relat.Elem.1991,63,193.
[17](a) Muruganantham,R.;Mobin,S.M.;Namboothiri,I.N.N.Org.Lett.2007,9,1125.(b) Alen,J.;Dobrzanska,L.;De Borggraeve,W.M.;Compemolle,F.J.Org.Chem.2007,72,1055.(c) Al Quntar,A.A.A.;Srivastava,H.K.;Srebnik,M.;Melman,A.;Ta-Shma,R.;Shurki,A.J.Org.Chem.2007,72,4932.(d) Moriguchi,T.;Yanagi,T.;Kunimori,M.;Wada,T.;Sekine,M.J.Org.Chem.2000,65,8229.
[18](a) Wu,J.;Sun,W.;Sun,X.;Xia,H.-G Green Chem.2006,8,365.(b) Wu,J.;Sun,W.;Xia,H.-G;Sun,X.Org.Biomol.Chem.2006,4,1663.
[19]Lewis Acids in Organic Synthesis,Edited by Yamamoto,H.Wiley-VCH VerlagGmbH,D-69469,Germany,2000.
[20]Yang,Y.;Ding,Q.P.;Wu,J.Tetrahedron 2008,64,1378.
[21]6.For selected examples,see:(a) Ma,J.;Cahard,D.Angew.Chem.Int.Ed.2004, 43,4566.(b) Groger,H.Chem.-Eur.J.2001,7,5246.(c) Shibasaki,M.;Sasai,H.;Arai,T.Angew.Chem.Int.Ed.Engl.1997,36,1236.(d) Matsui,K.;Takizawa,S.;Sasai,H.Synlett 2006,761.(e) Gryko,D.;Zimnicka,M.;Lipinski,R.J.Org.Chem.2007,72,964.
[22](a) Dalko,P.I.;Moisan,L.Angew.Chem.Int.Ed.2001,40,3726.(b)List,B.Tetrahedron 2002,58,5573.(c)Duthaler,R.O.Angew.Chem.Int.Ed.2003,42,975.(d) Dalko,P.I.;Moisan,L.Angew.Chem.Int.Ed.2004,43,5138.
[23](a) Ibrahem,I.;Cordova,A.Angew.Chem.Int.Ed.2006,45,1952.(b) Jellerichs,B.G.;Kong,J .R.;Krische,M.J.J.Am.Chem.Soc.2003,125,7758.(c) Trost,B.M.;McEachern,E.J.;Toste,F.D.J.Am.Chem.Soc.1998,120,12702.(d)Sawamura,M.;Sudoh,M.;Ito,Y.J.Am.Chem.Soc.1996,118,3309.
[1](a) Westheimer,F.H.Science 1987,235,1173.(b) Seto,H.;Kuzuyama,T.Nat.Prod Rep.1999,16,589.
[2]For examples of phosphorus compounds as pharmaceuticals,see:(a) Kafarski,P.;LeJczak,B.Curr.Med.Chem.:Anti-Cancer Agents 2001,7,301.(b) Colvin,O.M.Curr.Pharm.Des.1999,5,555.(c) Zon,G.Prog.Med.Chem.1982,19,205.
[3]For reviews of the biological activity of a-amino phosphonic acids,see:(a)Hiratake,J.;Oda,J.Biosci.Biotechnol.Biochem.1997,61,211.(b) Kafarski,P.;Lejczak,B.Phosphorus,Sulfur,Silicon 1991,63,193.
[4](a) Allen,J.G.;Atherton,F.R.;Lambert,R.W.;Nisbet,L.J.;Ringrose,P.S.Nature 1978,272,56.(b) Pratt,R.F.Science 1989,246,917.
[5]Maier,L.;Diel,P.J.Phosphorus,Sulfur,Silicon 1991,57,57.
(6) Beers,S.A.;Schwender,C.F.;Loughney,D.A.;Malloy,E.;Demarest,K.;Jordan,J.Bioorg.Med.Chem.1996,4,1693.
[7]Li,X.S.;Zhang,D.W.;Jiang,Y.Y.;Zhao,Y.F.Org.Lett.2005,7,4919.
[8](a) Wu,J.;Yang,Z.;Fathi,R.;Zhu,Q.;Wang,L.U.S.Patent No.6,703,514.(b)Wu,J.;Yang,Z.;Fathi,R.;Zhu,Q.U.S.Pat.Appl.Publ.2004,43 pp.
[9](a) Ma,C;Liu,X.;Li,X.;Yu,S.;Cook,J.M.J.Org.Chem.2001,66,4525.(b)Kondo,T.;Okada,T.;Suzuki,T.;Mitusudi,T.-a.J.Organomet.Chem.2001,622,149.(c) Muller,T.E.;Schmidtchen,F.P.Organometallics 2001,20,4384.
[10](a) Van Esseveldt,B.C.J.;Rutjes,F.P.J.T.Org.Lett.2003,5,1717.(b)Kozawa,Y.;Mori,M.Tetrahedron Lett.2002,43,1499.(c) Torres,J.C;Pilli,R.A.;Vargas,M.D.;Pinto,A.C.Tetrahedron 2002,58,4487.
[11](a) Roesch,K.R.;Larock,R.C.J.Org.Chem.2002,67,86.(b) Zhang,H.;Larock,R.C.Tetrahedron Lett.2002,43,1359.
[12](a) Melis,K.;Verpoort,F.Eur.J.Org.Chem.2002,22,3779.(b) Anastasia,L.;Xu,C;Negishi,E.-i.Tetrahedron Lett.2002,43,5673.(c) Bellina,F.;Ciucci,D.;Rossi,R.Tetrahedron 2000,56,2533.(d) Qing,F.L.;Gao,W.Z.Tetrahedron Lett.2000,41,7727.(e) Kundu,N.G.;Pal,M.;Nandi,B.J.Chem.Soc,Perkin Trans.1998,1,561.(f) Liao,H.Y.;Cheng,C.H.J.Org.Chem.1995,60,3711.(g) Ogawa,Y.;Maruno,M.;Wakamatsu,T.Heterocycles 1995,41,2587.
[13](a) Trost,B.M.;Rhee,Y.H.J.Am.Chem.Soc.2002,124,2528.(b) Bates,C.G.;SaeJueng,P.;Murphy,J.M.;Venkataraman,D.Org.Lett.2002,4,4727.(c) Cutchins,W.W.;McDonald,F.E.Org.Lett.2002,4,749.(d) Aschwanden,P.;Frantz,D.E.;Carreira,E.M.Org.Lett.2000,2,2331.(e) McDonald,F.E.;Reddy,K.S.;Diaz,Y. J.Am.Chem.Soc.2000,122,4304.
[14](a) Peng,A.Y.;Ding,Y.X.J.Am.Chem.Soc.2003,125,15006.(b) Tang,W.;Ding,Y.X.J.Org.Chem.2006,71,8489.(c) Peng,A.Y.;Ding,Y.X.Org.Lett.2005,7,3299.
[15]For examples,see:(a) Asao,N.;Yudha,S.S.;Nogami,T.;Yamamoto,Y.Angew.Chem.,Int.Ed.2005,44,5526.(b) Yanada,R.;Obika,S.;Kono,H.;Takemoto,Y.Angew.Chem.,Int.Ed.2006,45,3822.
[16](a) Wu,J.;Sun,W.;Sun,X.;Xia,H.-G.Green Chem.2006,8,365.(b) Wu,J.;Sun,W.;Xia,H.-G.;Sun,X.Org.Biomol.Chem.2006,4,1663.
[17]Dieltiens,N.;Stevens,C.V.Org.Lett.2007,9,465.
[18]Black,T.H.In Encyclopedia of Reagents for Organic Synthesis;Paquette,L.A.,Ed.;John Wiley & Sons:Chichester,UK,1995;Vol.6,p 4476.
[19]Zeni,R.G.;Larock,R.C.Chem.Rev.2006,106,4644.[20]For recent selected examples,see:(a) Srivastava,A.K.;Archana;Jaiswal,M.J.Indian Chem.Soc.2007,84,260.(b) Deng,Y.;Yang,D.C;Shen,Y.;Zhong,Y.G.Chin.Chem.Lett.2007,18,7.(c) Li,S.;Chiu,G.;Pulito,V.L.;Liu,J.;Connolly,P.J.;Middleton,S.A.Bioorg.Med.Chem.Lett.2007,17,1646.(d) Mailliet,P.;Bertin,L.;Benard,D.;Carrez,C;Vallee,F.;Bacque,E.Fr.Demande 2006,46.(e) Salman,M.;Anand,N.;Yadav,G.C;Sharma,S.;Kapkoti,G.S.;Chugh,A.;Nanda,K.PCTInt.Appl.2006,43 pp.(f) Rawat,U.B.;Rao,M.B.Eur.J.Biochem.1997,246,344.(g) Cochran,D.G.J.Econ.Entomol.1994,87,879;(h)Chem.Abstr.1995,122,233-234.(i) Abdou,W.M.;Kamel,A.A.;Khidre,M.D.Heteroatom Chem.2004,75,77.
[1](a) Nakajima,M.;Saito,M.;Shiro,M.;Hashimoto,S.-I.J.Am.Chem.Soc.1998,120,6419.
(b) Shimada,T.;Kina,A.;Ikeda,S.;Hayashi,T.Org.Lett.2002,4,2799.
(c) Malkov,A.V.;Orsini,M.;Pernazza,D.;Muir,K.W.;Langer,V.;Meghani,P.;Ko(?)ovsk(?),P.Org.Lett.2002,4,1047.
(d) Malkov,A.V.;Dufkov(?),L.;Farrugia,L.;Ko(?)ovsk(?),P.Angew.Chem.Int.Ed.2003,42,3674.)
[2](a) Collado,D.;Perez-Inestrosa,E.;Suau,R.J.Org.Chem.2003,68,3574.
(b)Collado,D.;Perez-Inestrosa,E.;Suau,R.;Desvergne,J.-P.;Bouas-Laurent,H.Org.Lett.2002,4,855.
(c) Collado,D.;Perez-lnestrosa,E.;Suau,R.;Navarrete,J.T.L.Tetrahedron 2006,62,2927.
(d) Durmaz,Y.Y.;Yilmaz,G.;Yagci,Y.J.Polym.Sci.,Part A.:Polym.Chem.2007,45,423.
[3](a) Cop(?)ret,C.;Adolfsson,H.;Chiang,J.P.;Yudin,A.K.;Sharpless,K.J.Org.Chem.1998,63,1740;
(b) Prasad,M.R.;Kamalakar,G.;Madhavi,G.;Kuikarni,S.J.;Raghavan,K.V.Chem.Commun.2000,1577.
[4]Daniel,C.;Ezequiel P.I.;Rafael,S.;Desvergne J.P.;Henri B.L.Org.Lett.,2002,4(5),855.
[5]Malkov,A.V.;Pedro,R.L.;Lada B.;Lubom(?)r,R.;丨Lenka,D.;Martin K.Zhu,F.;Pavel K.J.Am.Chem.Soc.,2008,130(15),5341.
[6]Antri,A.E.;Lachkar,M.Fitoterapia,2004,75,774.
[7]For selected examples,see:(a) Larock,R.C.In Acetylene Chemistry;Diederich,F.;Stang,P.J.;Tykwinski,R.R.,Eds.;Wiley-VCH:Weinheim,2005,51-99.
(b)Alonso,F.;Beletskaya,I.P.;Yus,M.Chem.Rev.2004,104,3079.
(c) Zeni,G.;Larock,R.C.Chem.Rev.2006,106,4644.
[8]For selected examples,see:(a) Ding,Q.;Wu,J.Org.Lett.2007,9,4959.
(b) Gao,K.;Wu,J.J Org.Chem.2007,72,8611.
(c) Sun,W.;Ding,Q.;Sun,X.;Fan,R.;Wu,J.J.Comb.Chem.2007,9,690.
(d) Ye,Y.;Ding,Q.;Wu,J.Tetrahedron 2008,64,1378.
[9](a) Huang,Q.;Larock,R.C.J.Org.Chem.2003,68,980.
(b) Dai,G.;Larock,R.C.J.Org.Chem.2003,68,920.
(c) Dai,G.;Larock,R.C.J.Org.Chem.2002,67,7042.
(d) Huang,Q.;Hunter,J.A.;Larock,R.C.J.Org.Chem.2002,67,3437.
(e)Roesch,K.R.;Larock,R.C.J.Org.Chem.2002,67,86.
(f) Roesch,K.R.;Zhang,H.;Larock,R.C.J.Org.Chem.2001,66,8042.
(g) Roesch,K.R.;Larock,R.C.Org.Lett.1999,1,553.
[10]For selected examples,see:(a) Bi,H.-P.;Guo,L.-N.;Duan,X.-H.;Gou,F.-R.; Huang,S.-H.;Liu,X.-Y.;Liang,Y.-M.Org.Lett.2007,9,397.
(b) Sniady,A.;Wheeler,K.A.;Dembinski,R.Org.Lett.2005,7,1769.
(c) Liu,Y.-H.;Song,F.-J.;Cong,L.Q.J.Org.Chem.2005,70,6999.
(d) Peng,A.Y.;Ding,Y.X.Org.Lett.2004,6,1119.
(e) Yue,D.;Yao,T.;Larock,R.C.J.Org.Chem.2005,70,10292.
[11]S.H.Yang,S.Chang,Org.Lett.2001,3,4209.
[12]Huo,Z.B.;Tomeba,H.;Yamamoto Y.Tetrahedron Lett.2008,49,5531.
[13]Yeom,H.-S.;Kim,S.;Shin,S.Synlett 2008,924.
[14](a) Young,I.S.;Kerr,M.A.Angew.Chem.Int.Ed.2003,42,3023.
(b) Young,1.S.;Kerr,M.A.Org.Lett.2004,6,139.
(c) Young,I.S.;Williams,J.L.;Kerr,M.A.Org.Lett.2005,7,953.
(d) Sibi,M.P.;Ma,Z.;Jasperse,C.P.J.Am.Chem.Soc.2005,127,5764.
(e) Kang,Y.-B.;Sun,X.-L.;Tang,Y.Angew.Chem.Int.Ed.2007,46,3918.
[15]Ganton,M.D.;Kerr,M.A.J.Org.Chem.2004,69,8554.
[16]Jensen,K.B.;Roberson,M.;Jφrgensen,K.A.J.Org.Chem.2000,65,9080
[17](a) Houk,K.N.;Sims,J.;Duke,R.E.;Strozier,R.W.;George,J.K.J.Am.Chem.Soc.1973,95,7287.
(b) Houk,K.N.;Sims,J.;Watts,C.R.;Luskus,L.J.J.Am.Chem.Soc.1973,95,7301.
(c) Sims,J.;Houk,K.N.J.Am.Chem.Soc.1973,95,5798.
[18]Lu,L.;Cao,W.;Chen,J.;Zhang,H.;Zhang,J.;J.Fluorine Chem.online
[19]For reviews,see:(a) Husinec,S.;Savic,V.Tetrahedron:Asymmetry 2005,16,2047.
(b) Kanemasa,S.Synlett 2002,1371.
(c) Gothelf,K.V.;Jφrgensen,K.A.Chem.ReV.1998,98,863.
(d) Pichon,M.;Figadere,B.Tetrahedron:Asymmetry 1996,7,927.
[20]Coskun,N.;Tuncman,S.Tetrahedron 2006,62,1345.
[1]Millonig,R.C.;Goldlust,M.B.;Maguire,W.E.;Rubin,B.;Schulze,E.;Wojnar,R.J.;Turkheimer,A.R.;Schreiber,W.F.;Brittain,R.J.J.Med.Chem.1973,16,780.
[2](a) Hari,A.;Miller,B.L.Org.Lett.2000,2,3667;
(b) Hull,R.;van den Broek,P.;Swain,M.L.J.Chem.Soc.,Perkin Trans.1 1975,922;For the synthesis of 4-aryl and unsubstituted 4H-3,1-benzothiazines.
(c) Nishio,T.J.Org.Chem.1997,62,1106;
(d)Schmidt,R.R.J.Heterocycl.Chem.1999,36,153;
(d) Ress,C.W.Synlett 1997,704;
(e) Pazdera,P.Molecules 2000,7,96;
(f) Schmittel M.Synthesis 2004,3,415.
[3](a) J.Quiroga,P.Hern(?)ndez,B.Insuasty,R.Abon(?),J.Cobo,A.S(?)nchez,M.Nogueras,J.N.Low,J.Chem.Soc.,Perkin Trans.1 2002,555;
(b) I.Hutchinson,S.A.Jennings,B.R.Vishnuvajjala,A.D.Westwell,M.F.G.Stevens,J.Med Chem.2002,45,744.
[4]E.F.Domino,K.R.Unna,J.Kerwin,J.Pharmacol.Exp.Ther.1952,105,486.
[5](a) J.Benavides,J.C.Camelin,N.Mitrani,F.Flamand,A.Uzan,J.J.Legrand,G.Le Fur,Neuropharmacology 1985,24,555;
(b) P.Jimonet,F.Audiau,M.Barreau,J.-C.Blanchard,J.-M.Stutzmann,S.Mignani,J.Med.Chem.1999,42,2828.
[6]W.Aelterman,Y.Lang,B.Willemsens,I.Vervest.S.Leurs,F.De Knaep,Org.Prep.Res.Dev.2001,5,467).
[7](a) L.L.Joyce,G.Evindar,R.A.Batey,Chem.Commun.2004,446;
(b) G.Evindar,R.A.Batey,J.Org.Chem.2006,71,1802。
[8]C.Ana;M.Ana.J.Heterocycl.Chem.,1999,36,991;
(b) Z.Le,J.Xu,H.Rao,M.Ying.J.Heterocycl.Chem.2006,434,1123;
(c) F.Dagmar;P.Pavel.Synthesis 2008,8,1297.
[9](a) E.Sperotto,G.P.M.van Klink,J.G.de Vries,G.van Koten,J.Org.Chem.2008,73,5625;
(b) J.Louie,J.F.Hartwig,J.Am.Chem.Soc.1995,117,11598;
(c) M.A.Fern(?)ndez-Rodriguez,Q.Shen,J.F.Hartwig,J.Am.Chem.Soc.2006,128,2180;
d) T.Kondo,T.-A.Mitsudo,Chem.Rev.2000,100,3205;
(e) C.G.Bates,R.K.Gujadhur,D.Venkataraman,Org.Lett.2002,4,2803;
(f) C.G.Bates,P.Saejueng,M.Q.Doherty,D.Venkataraman,Org.Lett.2004,6,5005;
(g) N.Taniguchi,J.Org.Chem.2004,69,6904;
(h) S.V.Ley,A.W.Thomas,Angew.Chem.2003,116,1061;Angew.Chem.Int.Ed.2003,42,5400;
(i) M.Murata,S.L.Buchwald,Tetrahedron 2004,60,7397;
(j) Y.-C.Wong,T.T.Jayanth,C.-H.Cheng,Org.Lett.2006,8,5613.
(b) Hung,D.T.;Jamison,T.F.;Schreiber,S.L.Chem.Biol.,1996,3,623-639.
[2]Fergus,S.;Bender,A.;Spring,D.R.Curr.Opin.Chem.Biol.,2005,9,304-309.
[3](a) Nicolaou,K.C.;Yang,Z.;Liu,J.-J.;Ueno,H.;Nantermet,P.G.;Guy,R.K.Nature 1994,367,630-634;
(b) Nicolaou,K.C.;Nantermet,P.G.;Ueno,H.;Guy,R.K.;Couladouros,E.A.;Sorensen,E.J.J.Am.Chem.Soc.1995,117,624-633;
(c)Nicolaou,K.C.;Liu,J.-J.;Yang,Z.;Ueno,H.;Sorensen,E.J.;Claiborne,C.F.;Guy,R.K.;Hwang,C.-K.;Nakada,M.;Nantermet,P.G.J.Am.Chem.Soc.1995,117,633-644;
(d) Nicolaou,K.C.;Yang,Z.;Liu,J.-J.;Nantermet,P.G.;Claiborne,C.F.;Renaud,J.;Guy,R.K.;Shibayama,K.;J.Am.Chem.Soc.1995,117,645-652;
(d)Nicolaou,K.C.;Ueno,H.;Liu,J.-J.;Nantermet,P.G.;Yang,Z.;Renaud,J.;Pauivannan,K.;Chadha,R.J.Am.Chem.Soc.1995,117,653-659.
[4]Tempest,P.A.;Armstrong,R.W.J.Am.Chem.Soc.1997,119,7607-7608.
[5]Marx,M.A.;Griliot,A-L;Louer,C.T.;Beaver,K.A.;Bartlett,P.A.J.Am.Chem.Soc.1997,119,6153-6167.
[6]Reayi,A.;Arya,P.Curr.Opin.Chem.Biol.2005,9(3),240-247.
[7]Schreiber,S.L.Science 2000,287,1964-1969.
[8](a) Shang,S.Y.;Tan,D.S.;Curt.Opin.Chem.Biol.2005,9(3),248-258;
(b)刘钢(Liu,G);李裕林(Li,Y.L.);南发俊(Nan,F.J.),化学进展(Progress in Chemistry),2006,18(6),734-742.
[9]Pelish,H.E.;Westwood,N.J.;Feng,Y;Shair,M.D.et al.J.Am.Chem.Soc.2001,123,6740-6741.
[10]Lo,M.M.C.;Neumann,C.S.;Nagayama,S.;Perlstein,E.O.;Schreiber,S.L.J.Am.Chem.Soc.2004,126,16077-16086.
[11]Ding,K.;Lu,Y.P.;Nikolovska-Coleska,Z.;Wang,S.M.et al.J.Am.Chem.Soc.2005,127,10130-10131.
[12](a) Nicolaou,K.C.;Pfefferkorn,J.A.;Roecker,A.J.;Cao,G.Q.;Barluenga,S.;Mitchell,H.J.J.Am.Chem.Soc.2000,122,9939-9953;
(b) Nicolaou,K.C.;Pfefferkorn,J.A.;Mitchell,H.J.;Roecker,A.J.;Barluenga,S.;Cao,G.Q.;Affleck,R.L.;Lillig,J.E.J.Am.Chem.Soc.2000,122,9954-9967;
(c)Nicolaou,K.C.;Pfefferkorn,J.A.;Barluenga,S.;Mitchell,H.J.;Roecker,A.J;Cao,G.Q.J.Am.Chem.Soc.,2000,122,9968-9976.
[13](a) Nicolaou,K.C.;Pfefferkorn,J.A.;Schuler,F.;Roecker,A.J.;Cao,G.Q.;Casida,J.E.Chem.Biol.2000,7,979-992.
[14]Nicolaou,K.C.;Roecker,A.J.;Barluenga,S.;Pfefferkorn,J.A.;Cao,G.Q.Chembiochem,2001,2,460-465.
[15]Nicolaou,K.C.;Evans,R.M;Roecker,A.J.;Hughes,R.;Downes,M.;Pfefferkorn,J.A.Org.Biomol.Chem.2003,/,908-920.
[16]Michael,J.P.Nat.Prod.Rep.2004,21,650-668.
[17](a) Arya,P.;Durieux,P.;Chen,Z.X.;Joseph,R.;Leek,D.M.J.Comb.Chem.2004,6,54-64;(b) Arya,P.Couve2Bonnaire,S.;Durieux,P.et al.J.Comb.Chem.2004,6,735-745;(c) Khadem,S.;Joseph,R.;Rastegar,M.;Oudatchin,K.A.;Arya,P.J.Comb.Chem.2004,6,724-734.
[18]Slee,D.H.;Bhat,A.S.;Nguyen,T.N.;Kish,M.;Lundeen,K.;Newman,M.J.;McConnell,S.J.J.Med.Chem.2003,46,1120-1122.
[19]Barun,O.;Sommer,S.;Waldmann,H.Angew.Chem.Int.Ed.2004,43,3195-3199.
[20](a)Sternson,S.M.;Louca,J.B.;Wong,J.C;Schreiber,S.L.J.Am.Chem.Soc.2001,123,1740-1747;(b) Wong,J.C;Sternson,S.M.;Louca,J.B.;Hong,R.;Schreiber,S.L.Chem.Biol.2004,11,1279-1291.
[21]Kuruvilla,F.G.;Shamji,A.F.;Sternson,S.M.;Hergenrother,P.J.;Schreiber,S.L.Nature,2002,416,653-657.
[22]Haggarty,S.J.;Koeller,K.M.;Wong,J.C;Grozinger,CM.;Schreiber,S.L.Proc.Natl.Acad.Sc.USA,2003,100,4389-4394.
[23]Taylor,S.J.;Taylor,A.M.;Schreiber,S.L.Angew.Chem.Int.Ed.2004,43,1681-1685.
[24]Weber,L.Curr.Med.Chem.2002,9(23),2085-2093.
[25]Povarov,L.S.;Mikhailov,B.M.;Izvestiya Akademii Nauk SSSR,Seriya Khimicheskaya,1963,955-956.
[26]Nicolaou,K.C.;Cao,G.Q.;Pfefferkorn,J.A.;Angew.Chem.Int.Ed.2000,39,739-743.
[27]Andreana,P.R.;Liu,C.C.;Schreiber,S.L.Org.Lett.2004,6,4231-4233.
[28]Tietze,L.F.;Rackelmann,N.;Sekar,G.Angew.Chem.In.Ed.2003,42,4254-4257.
[29]Young,I.S.;Kerr,M.A.Angew.Chem.Int.Ed.2003,42,3023-3026.
[30]Arya,P.;Joseph,R.;Gan,Z.G.;Rakic,B.Chemistry & Biology 2005,12,163 -180.
[31]Clardy,J.;Walsh,C.Nature,2004,432,829-837.
[32]Ho,T.Tactics of Organic Synthesis.Wiley,1994.
[33]Denmark,S.E.;Thorarensen,A.Chem Rev,1996,96(1),137.
[34]Kataoka,T.;Kinoshita,H.;Kinoshita,S.;Tatsunori,I.Tetrahedron Lett.2002,43,7039.
[35]Wang,W.;Li,H.;Wang,J.;Zu,L.S.J.Am.Chem.Soc.,2006,128(32),10354-10355.
[36]Stelmakh,A.;Stellfeld,T.;Kalesse,M.;Org.Lett.2006,8(16),3485-3488.
[37]Bogdanowicz-Szwed,K.;Gil,R.Monatsh.Chem.2004,135,1415.
[38]Ballini,R.;Buciano,L.;Fiorini,D.;Giarlo,G.Chem.Commun.2005,(20),2633.
[39]Ferna,M.;Alonso,R.Org.Lett.2005,7,11.
[40]Chen,Y.J.;Chen,C.M.;Lin,W.Y.Tetrahedron Lett,1993,34(18),2961.
[41]RamaRao,V.V.V.N.S.;Venkat-Reddy,G.;Maitraie,D.;Ravikanth,S.;Yadla,R.;Narsaiah,B.;Shanthan-Rao,P.Tetrahedron 2004,60,12231.
[42]Ram,V.J.;Goel,A.;Sarkhe,S.;Maulik,P.R.Bioorg.Med.Chem.2002,10,1275.
[43]Ewold,W.D.;Panella,L.;Pinho,P.;Maulik P.R.Tetrahedron 2004,60,9687.
[44]Glushkov,V.A.;Shurov,S.N.;Maioroval,O.A.;Postanogoval,G.A.Chem.Heterocycl.Compd.2001,37,444.
[45]Lin,Y.-L.;Kuo,H.-S.;Wang,Y.-W.;Huang,S.-T.Tetrahedron 2003,59,1277.
[46]Wang,J.-W.;Jia,J.;Hou,D.-J.;Li,H.-M.;Yin,J.Chin.J.Org.Chem.2003,23,173(in Chinese).(
王建武,贾炯,候殿杰,李红梅,尹军,有机化学,2003,23,173.)
[47]Mc-Dermott,P.J.;Stockman,R.A.Org.Lett.2005,7,27.
[48]De-Boeck,B.;Harrington-Frost,N.M.;Pattenden,G.Org.Biomol.Chem.2005,3,340.
[49]Handa,S.;Pattenden,G.Chem Comm un,19989,3,311.
[50]Majumdar,K.C.;Samanta,S.K.Tetrahedron Lett.2002,43,2119.
[51]Alcaide,B.;Almendros,P.;Aragoncillo,C.;Redondo,M.C.Eur.J.Org.Chem.2005,3,98.
[1]For selected examples,see:(a) Bentley,K.W.The Isoquinoline Alkaloids;Harwood Academic:Australia,1998;Vol 1.(b) Trotter,B.W.;Nanda,K.K.;Kett,N.R.;Regan,C.P.;Lynch,J.J.;Stump,G.L.;Kiss,L.;Wang,J.;Spencer,R.H.;Kane,S.A.;White,R.B.;Zhang,R.;Anderson,K.D.;Liverton,N.J.;Mclntyre,C.J.;Beshore,D.C;Hartman,G.D.;Dinsmore,C.J.J.Med.Chem.2006,49,6954.(c) Ramesh,P.;Reddy,N.S.;Venkateswarlu,Y.J.Nat.Prod 1999,62,780.(d) Oi,S.;Ikedou,K.;Takeuchi,K.;Ogino,M.;Banno,Y.;Tawada,H.;Yamane,T.PCT Int.Appl.2002,600 pp (WO 2002062764 Al).
[2]For selected examples,see:(a) Scott,J.D.;Williams,R.M.Chem.Rev.2002,102,1669.(b) Chan,C;Heid,R.;Zheng,S.;Guo,J.;Zhou,B.;Furuuchi,T.;Danishefsky,S.J.J.Am.Chem.Soc.2005,127,4596.(c) Magnus,P.;Matthews,K.S.J.Am.Chem.Soc.2005,127,12476.(d) Zheng,S.;Chan,C;Furuuchi,T.;Wright,B.J.D.;Zhou,B.;Guo,J.;Danishefsky,S.D.Angew.Chem.,Int.Ed.2006,45,1754.(e) Vincent,G.;Williams,R.M.Angew.Chem.,Int.Ed.2007,46,1517.
[3](a) Obika,S.;Kono,H.;Yasui,Y.;Yanada,R.;Takemoto,Y.J.Org.Chem.2007,72,4462.(b) Asao,N.;Yudha S.,S.;Nogami,T.;Yamamoto,Y.Angew.Chem.Int.Ed.2005,44,5526.(c) Yanada,R.;Obika,S.;Kono,H.;Takemoto,Y.Angew.Chem.Int.Ed.2006,45,3822.(d) Asao,N.;Iso,K.;Yudha S.,S.Org.Lett.2006,8,4149.(e) Mori,S.;Uerdingen,M.;Krause,N.;Morokuma,K.Angew.Chem.Int.Ed.2005,44,4715.(f) Asao,N.;Chan,C.S.;Takahashi,K.;Yamamoto,Y.Tetrahedron 2005,61,11322.(g) Ohtaka,M.;Nakamura,H.;Yamamoto,Y.Tetrahedron Lett.2004,45,7339.(h) Witulski,B.;Alayrac,C;Tevzadze-Saeftel,L.Angew.Chem.Int.Ed.2003,42,4257.(i) Yavari,I.;Ghazanfarpour-Darjani,M.;Sabbaghan,M.;Hossaini,Z.Tetrahedron Lett.2007,48,3749.(j) Shaabani,A.;Soleimani,E.;Khavasi,H.R.Tetrahedron Lett.2007,48,4743.(k) Wang,G.-W.;Li,J.-X.Org.Biomol.Chem.2006,4,4063.(1) Diaz,J.L.;Miguel,M.;Lavilla,R.J.Org.Chem.2004,69,3550.
[4](a) Huang,Q.;Larock,R.C.J.Org.Chem.2003,68,980.(b) Dai,G.;Larock,R.C.J.Org.Chem.2003,68,920.(c) Dai,G.;Larock,R.C.J.Org.Chem.2002,67,7042.(d) Huang,Q.;Hunter,J.A.;Larock,R.C.J.Org.Chem.2002,67,3437.(e)Roesch,K.R.;Larock,R.C.J.Org.Chem.2002,67,86.(f) Roesch,K.R.;Zhang,H.;Larock,R.C.J.Org.Chem.2001,66,8042.(g) Roesch,K.R.;Larock,R.C.Org.Lett.1999,1,553.
[5]Croisy-Delcey,M.;Croisy,A.;Carrez,D.;Huel,C;Chiaroni,A.;Ducrot,P.; Bisagni,E.;Jin,L.;Leclercq,G.Bioorg.Med.Chem.2000,8,2629.
[6]Whaley,W.M.;Govindachari,T.R.In Organic Reactions;Adams,R.,Ed.;Wiley:New York,1951;Vol.6,pp 151-190.
[7]Gensler,W.J.In Organic Reactions;Adams,R.,Ed.;Wiley:NewYork,1951;Vol.6,pp 191-206.
[8](a) Maassarani,F.;Pfeffer,M.;Le Borgne,G.J.Chem.Soc,Chem.Commun.1987,565.(b) Wu.G.;Geib.S.J.;Rheingold,A.L.;Heck,R.F.J.Org.Chem.1988,53,3288.(c) Girling,I.R.;Widdowson,D.A.Tetrahedron Lett.1982,23,4281.(d)Roesch,K.R.;Larock,R.C.J.Org.Chem.1998,63,5306.
[9]Dai,G.X.;Larock,R.C.,Org.Lett.,2001,3,4035;Dai,G.X.;Larock,R.C.,J.Org.Chem.2003,68,920-928
[10](a) Arcadi,A.;Cacchi,S.;Fabrizi,G.;Moro,L.Eur.J.Org.Chem.1999,64,1137.(b) Cacchi,S.;Fabrizi,G.;Pace,P.;Marinelli,F.Synlett 1999,5,620.(c)Arcadi,A.;Cacchi,S.;Carnicelli,V.;Marinelli,F.Tetrahedron 1994,50,437.
[11]Arcadi,A.;Cacchi,S.;Rosario,M.D.;Fabrizi,G.;Marinelli,F.J.Org.Chem.1996,61,9280.
[12]Dai,G.X.;Larock,R.C.,Org.Lett.,2002,4,193.
[13]Huang,Q.H.;Hunter,J.A.;Larock,R.C.Org.Lett.2001,3,2973.
[14]Su,S.;Porco,Jr.J.A.J.Am.Chem.Soc,2007,129,7744.
[15]Nakamura,H.;Saito,H.;Nanjo,M.Tetrahedron Lett.2008,49,2697.
[16](a) Engel,R.Handbook of Organophosphorus Chemistry;Marcel Dekker,Inc.:New York,1992.(b) Kafarski,P.;Lejczak,B.Phosphorus Sulfur Silicon Relat.Elem.1991,63,193.
[17](a) Muruganantham,R.;Mobin,S.M.;Namboothiri,I.N.N.Org.Lett.2007,9,1125.(b) Alen,J.;Dobrzanska,L.;De Borggraeve,W.M.;Compemolle,F.J.Org.Chem.2007,72,1055.(c) Al Quntar,A.A.A.;Srivastava,H.K.;Srebnik,M.;Melman,A.;Ta-Shma,R.;Shurki,A.J.Org.Chem.2007,72,4932.(d) Moriguchi,T.;Yanagi,T.;Kunimori,M.;Wada,T.;Sekine,M.J.Org.Chem.2000,65,8229.
[18](a) Wu,J.;Sun,W.;Sun,X.;Xia,H.-G Green Chem.2006,8,365.(b) Wu,J.;Sun,W.;Xia,H.-G;Sun,X.Org.Biomol.Chem.2006,4,1663.
[19]Lewis Acids in Organic Synthesis,Edited by Yamamoto,H.Wiley-VCH VerlagGmbH,D-69469,Germany,2000.
[20]Yang,Y.;Ding,Q.P.;Wu,J.Tetrahedron 2008,64,1378.
[21]6.For selected examples,see:(a) Ma,J.;Cahard,D.Angew.Chem.Int.Ed.2004, 43,4566.(b) Groger,H.Chem.-Eur.J.2001,7,5246.(c) Shibasaki,M.;Sasai,H.;Arai,T.Angew.Chem.Int.Ed.Engl.1997,36,1236.(d) Matsui,K.;Takizawa,S.;Sasai,H.Synlett 2006,761.(e) Gryko,D.;Zimnicka,M.;Lipinski,R.J.Org.Chem.2007,72,964.
[22](a) Dalko,P.I.;Moisan,L.Angew.Chem.Int.Ed.2001,40,3726.(b)List,B.Tetrahedron 2002,58,5573.(c)Duthaler,R.O.Angew.Chem.Int.Ed.2003,42,975.(d) Dalko,P.I.;Moisan,L.Angew.Chem.Int.Ed.2004,43,5138.
[23](a) Ibrahem,I.;Cordova,A.Angew.Chem.Int.Ed.2006,45,1952.(b) Jellerichs,B.G.;Kong,J .R.;Krische,M.J.J.Am.Chem.Soc.2003,125,7758.(c) Trost,B.M.;McEachern,E.J.;Toste,F.D.J.Am.Chem.Soc.1998,120,12702.(d)Sawamura,M.;Sudoh,M.;Ito,Y.J.Am.Chem.Soc.1996,118,3309.
[1](a) Westheimer,F.H.Science 1987,235,1173.(b) Seto,H.;Kuzuyama,T.Nat.Prod Rep.1999,16,589.
[2]For examples of phosphorus compounds as pharmaceuticals,see:(a) Kafarski,P.;LeJczak,B.Curr.Med.Chem.:Anti-Cancer Agents 2001,7,301.(b) Colvin,O.M.Curr.Pharm.Des.1999,5,555.(c) Zon,G.Prog.Med.Chem.1982,19,205.
[3]For reviews of the biological activity of a-amino phosphonic acids,see:(a)Hiratake,J.;Oda,J.Biosci.Biotechnol.Biochem.1997,61,211.(b) Kafarski,P.;Lejczak,B.Phosphorus,Sulfur,Silicon 1991,63,193.
[4](a) Allen,J.G.;Atherton,F.R.;Lambert,R.W.;Nisbet,L.J.;Ringrose,P.S.Nature 1978,272,56.(b) Pratt,R.F.Science 1989,246,917.
[5]Maier,L.;Diel,P.J.Phosphorus,Sulfur,Silicon 1991,57,57.
(6) Beers,S.A.;Schwender,C.F.;Loughney,D.A.;Malloy,E.;Demarest,K.;Jordan,J.Bioorg.Med.Chem.1996,4,1693.
[7]Li,X.S.;Zhang,D.W.;Jiang,Y.Y.;Zhao,Y.F.Org.Lett.2005,7,4919.
[8](a) Wu,J.;Yang,Z.;Fathi,R.;Zhu,Q.;Wang,L.U.S.Patent No.6,703,514.(b)Wu,J.;Yang,Z.;Fathi,R.;Zhu,Q.U.S.Pat.Appl.Publ.2004,43 pp.
[9](a) Ma,C;Liu,X.;Li,X.;Yu,S.;Cook,J.M.J.Org.Chem.2001,66,4525.(b)Kondo,T.;Okada,T.;Suzuki,T.;Mitusudi,T.-a.J.Organomet.Chem.2001,622,149.(c) Muller,T.E.;Schmidtchen,F.P.Organometallics 2001,20,4384.
[10](a) Van Esseveldt,B.C.J.;Rutjes,F.P.J.T.Org.Lett.2003,5,1717.(b)Kozawa,Y.;Mori,M.Tetrahedron Lett.2002,43,1499.(c) Torres,J.C;Pilli,R.A.;Vargas,M.D.;Pinto,A.C.Tetrahedron 2002,58,4487.
[11](a) Roesch,K.R.;Larock,R.C.J.Org.Chem.2002,67,86.(b) Zhang,H.;Larock,R.C.Tetrahedron Lett.2002,43,1359.
[12](a) Melis,K.;Verpoort,F.Eur.J.Org.Chem.2002,22,3779.(b) Anastasia,L.;Xu,C;Negishi,E.-i.Tetrahedron Lett.2002,43,5673.(c) Bellina,F.;Ciucci,D.;Rossi,R.Tetrahedron 2000,56,2533.(d) Qing,F.L.;Gao,W.Z.Tetrahedron Lett.2000,41,7727.(e) Kundu,N.G.;Pal,M.;Nandi,B.J.Chem.Soc,Perkin Trans.1998,1,561.(f) Liao,H.Y.;Cheng,C.H.J.Org.Chem.1995,60,3711.(g) Ogawa,Y.;Maruno,M.;Wakamatsu,T.Heterocycles 1995,41,2587.
[13](a) Trost,B.M.;Rhee,Y.H.J.Am.Chem.Soc.2002,124,2528.(b) Bates,C.G.;SaeJueng,P.;Murphy,J.M.;Venkataraman,D.Org.Lett.2002,4,4727.(c) Cutchins,W.W.;McDonald,F.E.Org.Lett.2002,4,749.(d) Aschwanden,P.;Frantz,D.E.;Carreira,E.M.Org.Lett.2000,2,2331.(e) McDonald,F.E.;Reddy,K.S.;Diaz,Y. J.Am.Chem.Soc.2000,122,4304.
[14](a) Peng,A.Y.;Ding,Y.X.J.Am.Chem.Soc.2003,125,15006.(b) Tang,W.;Ding,Y.X.J.Org.Chem.2006,71,8489.(c) Peng,A.Y.;Ding,Y.X.Org.Lett.2005,7,3299.
[15]For examples,see:(a) Asao,N.;Yudha,S.S.;Nogami,T.;Yamamoto,Y.Angew.Chem.,Int.Ed.2005,44,5526.(b) Yanada,R.;Obika,S.;Kono,H.;Takemoto,Y.Angew.Chem.,Int.Ed.2006,45,3822.
[16](a) Wu,J.;Sun,W.;Sun,X.;Xia,H.-G.Green Chem.2006,8,365.(b) Wu,J.;Sun,W.;Xia,H.-G.;Sun,X.Org.Biomol.Chem.2006,4,1663.
[17]Dieltiens,N.;Stevens,C.V.Org.Lett.2007,9,465.
[18]Black,T.H.In Encyclopedia of Reagents for Organic Synthesis;Paquette,L.A.,Ed.;John Wiley & Sons:Chichester,UK,1995;Vol.6,p 4476.
[19]Zeni,R.G.;Larock,R.C.Chem.Rev.2006,106,4644.[20]For recent selected examples,see:(a) Srivastava,A.K.;Archana;Jaiswal,M.J.Indian Chem.Soc.2007,84,260.(b) Deng,Y.;Yang,D.C;Shen,Y.;Zhong,Y.G.Chin.Chem.Lett.2007,18,7.(c) Li,S.;Chiu,G.;Pulito,V.L.;Liu,J.;Connolly,P.J.;Middleton,S.A.Bioorg.Med.Chem.Lett.2007,17,1646.(d) Mailliet,P.;Bertin,L.;Benard,D.;Carrez,C;Vallee,F.;Bacque,E.Fr.Demande 2006,46.(e) Salman,M.;Anand,N.;Yadav,G.C;Sharma,S.;Kapkoti,G.S.;Chugh,A.;Nanda,K.PCTInt.Appl.2006,43 pp.(f) Rawat,U.B.;Rao,M.B.Eur.J.Biochem.1997,246,344.(g) Cochran,D.G.J.Econ.Entomol.1994,87,879;(h)Chem.Abstr.1995,122,233-234.(i) Abdou,W.M.;Kamel,A.A.;Khidre,M.D.Heteroatom Chem.2004,75,77.
[1](a) Nakajima,M.;Saito,M.;Shiro,M.;Hashimoto,S.-I.J.Am.Chem.Soc.1998,120,6419.
(b) Shimada,T.;Kina,A.;Ikeda,S.;Hayashi,T.Org.Lett.2002,4,2799.
(c) Malkov,A.V.;Orsini,M.;Pernazza,D.;Muir,K.W.;Langer,V.;Meghani,P.;Ko(?)ovsk(?),P.Org.Lett.2002,4,1047.
(d) Malkov,A.V.;Dufkov(?),L.;Farrugia,L.;Ko(?)ovsk(?),P.Angew.Chem.Int.Ed.2003,42,3674.)
[2](a) Collado,D.;Perez-Inestrosa,E.;Suau,R.J.Org.Chem.2003,68,3574.
(b)Collado,D.;Perez-Inestrosa,E.;Suau,R.;Desvergne,J.-P.;Bouas-Laurent,H.Org.Lett.2002,4,855.
(c) Collado,D.;Perez-lnestrosa,E.;Suau,R.;Navarrete,J.T.L.Tetrahedron 2006,62,2927.
(d) Durmaz,Y.Y.;Yilmaz,G.;Yagci,Y.J.Polym.Sci.,Part A.:Polym.Chem.2007,45,423.
[3](a) Cop(?)ret,C.;Adolfsson,H.;Chiang,J.P.;Yudin,A.K.;Sharpless,K.J.Org.Chem.1998,63,1740;
(b) Prasad,M.R.;Kamalakar,G.;Madhavi,G.;Kuikarni,S.J.;Raghavan,K.V.Chem.Commun.2000,1577.
[4]Daniel,C.;Ezequiel P.I.;Rafael,S.;Desvergne J.P.;Henri B.L.Org.Lett.,2002,4(5),855.
[5]Malkov,A.V.;Pedro,R.L.;Lada B.;Lubom(?)r,R.;丨Lenka,D.;Martin K.Zhu,F.;Pavel K.J.Am.Chem.Soc.,2008,130(15),5341.
[6]Antri,A.E.;Lachkar,M.Fitoterapia,2004,75,774.
[7]For selected examples,see:(a) Larock,R.C.In Acetylene Chemistry;Diederich,F.;Stang,P.J.;Tykwinski,R.R.,Eds.;Wiley-VCH:Weinheim,2005,51-99.
(b)Alonso,F.;Beletskaya,I.P.;Yus,M.Chem.Rev.2004,104,3079.
(c) Zeni,G.;Larock,R.C.Chem.Rev.2006,106,4644.
[8]For selected examples,see:(a) Ding,Q.;Wu,J.Org.Lett.2007,9,4959.
(b) Gao,K.;Wu,J.J Org.Chem.2007,72,8611.
(c) Sun,W.;Ding,Q.;Sun,X.;Fan,R.;Wu,J.J.Comb.Chem.2007,9,690.
(d) Ye,Y.;Ding,Q.;Wu,J.Tetrahedron 2008,64,1378.
[9](a) Huang,Q.;Larock,R.C.J.Org.Chem.2003,68,980.
(b) Dai,G.;Larock,R.C.J.Org.Chem.2003,68,920.
(c) Dai,G.;Larock,R.C.J.Org.Chem.2002,67,7042.
(d) Huang,Q.;Hunter,J.A.;Larock,R.C.J.Org.Chem.2002,67,3437.
(e)Roesch,K.R.;Larock,R.C.J.Org.Chem.2002,67,86.
(f) Roesch,K.R.;Zhang,H.;Larock,R.C.J.Org.Chem.2001,66,8042.
(g) Roesch,K.R.;Larock,R.C.Org.Lett.1999,1,553.
[10]For selected examples,see:(a) Bi,H.-P.;Guo,L.-N.;Duan,X.-H.;Gou,F.-R.; Huang,S.-H.;Liu,X.-Y.;Liang,Y.-M.Org.Lett.2007,9,397.
(b) Sniady,A.;Wheeler,K.A.;Dembinski,R.Org.Lett.2005,7,1769.
(c) Liu,Y.-H.;Song,F.-J.;Cong,L.Q.J.Org.Chem.2005,70,6999.
(d) Peng,A.Y.;Ding,Y.X.Org.Lett.2004,6,1119.
(e) Yue,D.;Yao,T.;Larock,R.C.J.Org.Chem.2005,70,10292.
[11]S.H.Yang,S.Chang,Org.Lett.2001,3,4209.
[12]Huo,Z.B.;Tomeba,H.;Yamamoto Y.Tetrahedron Lett.2008,49,5531.
[13]Yeom,H.-S.;Kim,S.;Shin,S.Synlett 2008,924.
[14](a) Young,I.S.;Kerr,M.A.Angew.Chem.Int.Ed.2003,42,3023.
(b) Young,1.S.;Kerr,M.A.Org.Lett.2004,6,139.
(c) Young,I.S.;Williams,J.L.;Kerr,M.A.Org.Lett.2005,7,953.
(d) Sibi,M.P.;Ma,Z.;Jasperse,C.P.J.Am.Chem.Soc.2005,127,5764.
(e) Kang,Y.-B.;Sun,X.-L.;Tang,Y.Angew.Chem.Int.Ed.2007,46,3918.
[15]Ganton,M.D.;Kerr,M.A.J.Org.Chem.2004,69,8554.
[16]Jensen,K.B.;Roberson,M.;Jφrgensen,K.A.J.Org.Chem.2000,65,9080
[17](a) Houk,K.N.;Sims,J.;Duke,R.E.;Strozier,R.W.;George,J.K.J.Am.Chem.Soc.1973,95,7287.
(b) Houk,K.N.;Sims,J.;Watts,C.R.;Luskus,L.J.J.Am.Chem.Soc.1973,95,7301.
(c) Sims,J.;Houk,K.N.J.Am.Chem.Soc.1973,95,5798.
[18]Lu,L.;Cao,W.;Chen,J.;Zhang,H.;Zhang,J.;J.Fluorine Chem.online
[19]For reviews,see:(a) Husinec,S.;Savic,V.Tetrahedron:Asymmetry 2005,16,2047.
(b) Kanemasa,S.Synlett 2002,1371.
(c) Gothelf,K.V.;Jφrgensen,K.A.Chem.ReV.1998,98,863.
(d) Pichon,M.;Figadere,B.Tetrahedron:Asymmetry 1996,7,927.
[20]Coskun,N.;Tuncman,S.Tetrahedron 2006,62,1345.
[1]Millonig,R.C.;Goldlust,M.B.;Maguire,W.E.;Rubin,B.;Schulze,E.;Wojnar,R.J.;Turkheimer,A.R.;Schreiber,W.F.;Brittain,R.J.J.Med.Chem.1973,16,780.
[2](a) Hari,A.;Miller,B.L.Org.Lett.2000,2,3667;
(b) Hull,R.;van den Broek,P.;Swain,M.L.J.Chem.Soc.,Perkin Trans.1 1975,922;For the synthesis of 4-aryl and unsubstituted 4H-3,1-benzothiazines.
(c) Nishio,T.J.Org.Chem.1997,62,1106;
(d)Schmidt,R.R.J.Heterocycl.Chem.1999,36,153;
(d) Ress,C.W.Synlett 1997,704;
(e) Pazdera,P.Molecules 2000,7,96;
(f) Schmittel M.Synthesis 2004,3,415.
[3](a) J.Quiroga,P.Hern(?)ndez,B.Insuasty,R.Abon(?),J.Cobo,A.S(?)nchez,M.Nogueras,J.N.Low,J.Chem.Soc.,Perkin Trans.1 2002,555;
(b) I.Hutchinson,S.A.Jennings,B.R.Vishnuvajjala,A.D.Westwell,M.F.G.Stevens,J.Med Chem.2002,45,744.
[4]E.F.Domino,K.R.Unna,J.Kerwin,J.Pharmacol.Exp.Ther.1952,105,486.
[5](a) J.Benavides,J.C.Camelin,N.Mitrani,F.Flamand,A.Uzan,J.J.Legrand,G.Le Fur,Neuropharmacology 1985,24,555;
(b) P.Jimonet,F.Audiau,M.Barreau,J.-C.Blanchard,J.-M.Stutzmann,S.Mignani,J.Med.Chem.1999,42,2828.
[6]W.Aelterman,Y.Lang,B.Willemsens,I.Vervest.S.Leurs,F.De Knaep,Org.Prep.Res.Dev.2001,5,467).
[7](a) L.L.Joyce,G.Evindar,R.A.Batey,Chem.Commun.2004,446;
(b) G.Evindar,R.A.Batey,J.Org.Chem.2006,71,1802。
[8]C.Ana;M.Ana.J.Heterocycl.Chem.,1999,36,991;
(b) Z.Le,J.Xu,H.Rao,M.Ying.J.Heterocycl.Chem.2006,434,1123;
(c) F.Dagmar;P.Pavel.Synthesis 2008,8,1297.
[9](a) E.Sperotto,G.P.M.van Klink,J.G.de Vries,G.van Koten,J.Org.Chem.2008,73,5625;
(b) J.Louie,J.F.Hartwig,J.Am.Chem.Soc.1995,117,11598;
(c) M.A.Fern(?)ndez-Rodriguez,Q.Shen,J.F.Hartwig,J.Am.Chem.Soc.2006,128,2180;
d) T.Kondo,T.-A.Mitsudo,Chem.Rev.2000,100,3205;
(e) C.G.Bates,R.K.Gujadhur,D.Venkataraman,Org.Lett.2002,4,2803;
(f) C.G.Bates,P.Saejueng,M.Q.Doherty,D.Venkataraman,Org.Lett.2004,6,5005;
(g) N.Taniguchi,J.Org.Chem.2004,69,6904;
(h) S.V.Ley,A.W.Thomas,Angew.Chem.2003,116,1061;Angew.Chem.Int.Ed.2003,42,5400;
(i) M.Murata,S.L.Buchwald,Tetrahedron 2004,60,7397;
(j) Y.-C.Wong,T.T.Jayanth,C.-H.Cheng,Org.Lett.2006,8,5613.