一些含1,2,3-三唑多结构化合物的合成与研究
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摘要
1H-1,2,3-三唑衍生物是一类具有广泛生物活性的化合物,它们被广泛应用在工业、农业、医学等领域。由于具有广泛的应用前景,化学家们对此类化合物的研究越来越多,新的有意义的化合物不断地被合成出来。基于此,在本论文中,我们合成了一些新的含有1,2,3-三唑的杂环化合物并进行研究和探讨。
本论文主要分以下两部分:
第一:文献综述部分。对1,3,4-噻二唑并[3,2-a]嘧啶酮、吡唑、吡啶和KF/Al_2O_3催化的麦克尔反应的研究现状及发展动态等做了简单的阐述。
第二:实验部分。主要工作分为四个部分。
1.P_2O_5-HCOOH催化的定向多样性合成2-(5-甲基-1-芳基-1H-1,2,3-三唑-4基)-5H-[1,3,4]噻二唑并[3,2-a]嘧啶-5-酮。
2.5-芳基-3-(1H-1,2,3-三唑-4-基)-1-(4-苯基噻唑-2-基)-4,5-二氢吡唑的合成。
3.化学选择性合成6-烷氧基-4-芳基-2-(1H-1,2,3-三唑-4-基)-5-氰基吡啶和2-氨基-6-芳基-4-(1H-1,2,3-三唑-4-基)异酞氰。
4.KF-Al_2O_3催化的丙二氰和α,β-不饱和酮的氰氢化反应。
1H-1,2,3-triazole derivatives are one type of chemical compound that haves widely biological activities and extensive use to industry,agriculture and medicine and so on.Based on their vast foreground,the compounds are researched by more and more chemists,and many novel significant compounds were synthesized.Seeing that the above-mentioned,some new heterocyclic compounds which contain 1,2,3-triazole nucleus were synthesized and studied in this thesis.
There are two major parts in this thesis:
The first part is about literature review.The research status and development of the 1,3,4-thiadiazolo[3,2-a]pyrimidinone,pyrazole,pyridine,and KF-Al_2O_3 catalyzed machael reaction.
The second part is about experiment sections.Major work is as follows:
1.P_2O_5-HCOOH catalyzed Diversity-Oriented Synthesis of 2-(1-Aryl-5-methyl-1H-1,2,3-triazol-4-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives.
2.Synthesis of 5-Aryl-4,5-dihydro-3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-1-(4-phenylthiazol-2-yl)pyrazoles.
3.Chemical selective synthesis of 6-Alkoxy-4-aryl-2-(1-aryl-5-methyl-1H-1,2,3-tri azol-4-yl)-5-cyanopyridines and 2-amino-6-aryl-4-(1-aryl-5-methyl-1H-1,2,3-tri azol-4-yl)isophthalonitriles.
4.KF-Al_2O_3 catalyzed conjugate hydrocyanation ofα,β-unsaturated ketones with malononitrile.
本论文主要分以下两部分:
第一:文献综述部分。对1,3,4-噻二唑并[3,2-a]嘧啶酮、吡唑、吡啶和KF/Al_2O_3催化的麦克尔反应的研究现状及发展动态等做了简单的阐述。
第二:实验部分。主要工作分为四个部分。
1.P_2O_5-HCOOH催化的定向多样性合成2-(5-甲基-1-芳基-1H-1,2,3-三唑-4基)-5H-[1,3,4]噻二唑并[3,2-a]嘧啶-5-酮。
2.5-芳基-3-(1H-1,2,3-三唑-4-基)-1-(4-苯基噻唑-2-基)-4,5-二氢吡唑的合成。
3.化学选择性合成6-烷氧基-4-芳基-2-(1H-1,2,3-三唑-4-基)-5-氰基吡啶和2-氨基-6-芳基-4-(1H-1,2,3-三唑-4-基)异酞氰。
4.KF-Al_2O_3催化的丙二氰和α,β-不饱和酮的氰氢化反应。
1H-1,2,3-triazole derivatives are one type of chemical compound that haves widely biological activities and extensive use to industry,agriculture and medicine and so on.Based on their vast foreground,the compounds are researched by more and more chemists,and many novel significant compounds were synthesized.Seeing that the above-mentioned,some new heterocyclic compounds which contain 1,2,3-triazole nucleus were synthesized and studied in this thesis.
There are two major parts in this thesis:
The first part is about literature review.The research status and development of the 1,3,4-thiadiazolo[3,2-a]pyrimidinone,pyrazole,pyridine,and KF-Al_2O_3 catalyzed machael reaction.
The second part is about experiment sections.Major work is as follows:
1.P_2O_5-HCOOH catalyzed Diversity-Oriented Synthesis of 2-(1-Aryl-5-methyl-1H-1,2,3-triazol-4-yl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives.
2.Synthesis of 5-Aryl-4,5-dihydro-3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-1-(4-phenylthiazol-2-yl)pyrazoles.
3.Chemical selective synthesis of 6-Alkoxy-4-aryl-2-(1-aryl-5-methyl-1H-1,2,3-tri azol-4-yl)-5-cyanopyridines and 2-amino-6-aryl-4-(1-aryl-5-methyl-1H-1,2,3-tri azol-4-yl)isophthalonitriles.
4.KF-Al_2O_3 catalyzed conjugate hydrocyanation ofα,β-unsaturated ketones with malononitrile.
引文
1 Japan Patent Application No.63-107949(1987).
2 US Patent No.4742063(1987).
3 US Patent No.4866064(1989).
4 Suiko,I.;Hayashida,S.and Nakatsu,S.Agric.Biol.Chem.,1982,46(11),2691-2695.
5 Okabe,T.;Maekawa,K.and Taniguchi,E.Agric.Biol.Chem.,1973,37,1197.
6 Tsuji,T.and Ueda,T.Chem.Pharm.Bull.,1974,22,471.
7 Tsuji,T.and Otsuka,Y.Heterocycles,1980,14,197.
8 Okabe,T.;Taniguchi,E.and K.Maekawa,Bull.Chem.Soc.Jpn.,1974,47,2813.
9 Okabe,T.;Mackawa,K.and Taniguchi,E.Agr.Biol.Chem,1973,37,1197.
10 Tsuji,T.and Takenaka,K.Bull.Chem.Soc.Japan,1982,55,637-638.
11 Takenaka,K.and Tsuji,T.J.Heterocyclic Chem,1996,33,1367-1370.
12 Gabriel,K.;Marks,P.J.and Constance,G.C,J.Org.Chem.,1980,45(24),4680-4683.
13 Shafiee,A.and Lalezari,I.,J.Heterocyclic.Chem.,1975,12,675.
14 Kuderna J.G.;Skiles,R.D.and Pilgram,K.,J.Org.Chem.,1971,36,3506.
15 Doad,G..J.;Okor,D.I.and Scheinmann,F.J.Chem.Soc.Perkin Trans1,1988,2933.
16 Lauer,R.F.and Zenchoff,G.J.Heterocyclic.Chem.,1976,13,291.
17 Kornis,G..Marks,P.J.and Chidester,C.G.,J.Org.Chem.,1980,45,4860-4863.
18 European Patent Application No.87103967.3(1987).
19 Salimov,T.M.;Kukaniev,M.A.;Sattorov,I.T.and Osimov,D.M.Pharma Chem J 2005,39,6,311-312.
20 Saifidin,Safarov.;Muhamacho,A.Kukaniev,:Elena,Karpuk and Herbert,Meier,J.Heterocycl.Chem 2007,44,269-271.
21 Katritzky,A.R.,Rees,C.W.,Scriven,E.F.V.,Elguero J.,Comprehensive Heterocyclic Chemistry,Pergamon,Oxford,1996,3,1-75.
22 Cottineau,B.,Toto,P.,Marot,C.,Pipaud,A.,Chenault,J.,Bioorg.Med.Chem.Lett.2002,12,2105-2108.
23 Lee,K.Y.,Kim,J.M.,Kim,J.N.,Tetrahedron Lett.2003,44,6737-6740.
24 Ranatunge R.R.,Earl R.A.,Garvey D.S.,Janero D.R.,Gordon L.L.,Allison M.M.,Murty M.G.,Richardson S.K.,Schwalb D.J.,Young D.V.and Zemtseva I.S.,Bioorg. Med.Chem.Lett., 2004,14,6049-6052
25 Ranatunge R.R., Augustyniak M., Bandarage U.K., Earl R.A., Ellis J.L., Garvey D.S.,Janero D.R., Letts L.G., Martino A.M., Murty M.G., Richardson S.K., Schroeder J.D.,Shumway M.J., William S.T., Trocha A.M., and Young D.V., J.Med.Chem.2004,47,2180-2193.
26 Feldmann, M.B., Fionula M., Maini, R.N., Annu.Rev.Immunol.1996,14, 397-440.
27 Regan J., Breitfelder S., Cirillo P., Gilmore T., Graham A.G., Hickey E., Klaus B.,Madwed J., Moriak M., Moss N., Pargellis C, Pav S., Proto A., Swinamer A., Tong L., and Torcellini C, J.Med.Chem.2002,45, 2994-3008.
28 Regan J., Capolino A., Cirillo P.F., Gilmore T., Graham A.G., Hickey E., Kroe R.R.,Madwed J., Moriak M., Nelson R., Pargellis C.A., Swinamer A., Torcellini C, Tsang M.,and Moss N., J.Med.Chem.2003,46, 4676-4686.
29 Goldstein D.M., Alfredson T., Bertrand J., Browner M.F., Clifford K., Dalrymple S.A.,Dunn J., Moar J.F., Harris S., Labadie S.S., Fargue J.L., Lapierre J.M., Larrabee S., Li F., Papp E., WeeneyD.M., Ramesha C, Roberts R., Rotstein D., Pablo B.S., Sjogren E.B., So O.Y., Talamas F.X., Tao W., Trejo A., Villasenor A., Welch M., Welch T., Weller P., Whiteley P.E., Young K., and Zipfel S., J.Med.Chem.2006,49, 1562-1575.
30 Tanitame A., Oyamada Y., Ofuji K., Fujimoto M., Iwai N., Hiyama Y., Suzuki K., Ito H., Terauchi H., Kawasaki M., Nagai K., Wachi M., and Yamagishi J., J.Med.Chem.2004,47, 3693-3696.
31 Wei F., Zhao B.X., Huang B., Zhang L., Sun C.H., Dong W.L., Shin D.S.and Miao J.Y., Bioorg.Med.Chem.Lett.2006,16, 6342-6347.
32 Ho C.Y., Ludovici D.W., Maharoof U.S.M., Mei J., Sechler J.L., Tuman R.W., Strobel E.D., Andraka L., Yen H.K., Leo G., Li J, Almond H., Lu H., DeVine A., Tominovich R.M., Baker J., Emanuel S., Gruninger R.H., Middleton S.A., Johnson D.L., and Galemmo R.A., Jr., J.Med.Chem.2005,48, 8163-8173.
33 Pinto D.J.P., Orwat M.J., Wang S., Fevig J.M., Quan M.L., Amparo E., Cacciola J.,Rossi K.A., Alexander R.S., Smallwood A.M., Luettgen J.M., Liang L., Aungst B.J.,Wright M.R., Knabb R.M., Wong P.C, Wexler R.R., and Lam P.Y.S., J.Med.Chem.2001,44, 566-578.
34 Pruitt J.R.,Pinto D.J.P.,Galemmo R.A.,Jr.,Alexander R.S.,Rossi K.A.,Wells B.L.,Drummond S.,Bostrom L.L.,Burdick D.,Bruckner R.,Chen H.,Smallwood A.,Wong P.C.,Wright M.R.,Bai S.,Luettgen J.M.,Knabb R.M.,Lam P.Y.S.,and Wexler R.R.,J.Med.Chem.2003,46,5298-5315.
35 Jia,Z.J.,Wu,Y.,Huang,W.,Zhang,P.,Song,Y.,Woolfrey,J.,Sinha,U.,Arfsten,A.E.,Edwards,S.T.,Hutchaleelaha,A.,Hollennbach,S.J.,Lambing,J.L.,Scarborough,R.M.,Zhu,B.Y.Bioorg.Med.Chem.Lett.,2004,14,1229-1234.
36 Thompson H.A.,Swanson C.P.and Norman A.G.,Gazz,107:476(1946)[C.A.,41,3774;(1947)].
37 George L.M.,Norman K.S.,Phytopathology,1949,39,721-751.CA,44:781h
38 Norman K.S.,US 2510724,1950,CA,44:8375h
39 Gysin H.and Margot A.US Patent 2,754,244(1956).
40 Shigematsbl M.,EP 355,409(1989),CA,112:139041p
41 Yoshiaki K,Japan pesticide Information,1988,53,27-31.
42 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,57-60.
43 Tomlin C.D.S.,The Pesticide Manual(12th ed.),British Crop Council,Surrey,UK,2000,795.
44 Ikeda K.,Sugaya K.,Coh A.,Chemical Regulation of Plants,1986,21(2),152-163.
45 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,41-43.
46 Kogyok Y.K.,JP 57-38,705,CA,97:51218n.
47 Takao K.,1980,JP 35035,CA,93,20 750t.
48 Takao K.,1980,JP 35038,CA,93,20 752v.
49 Tice C.M.,Musco V.A.,Roemmele,R.C.,Warner,H.L.,1995,US 5,453,414.
50 Hartfiel,U.,Dorfmeister,G.,Frake,H.,Geisler,J.,Johann,G.,Rees,R.,1993,US 5,405,829.
51 Marks M.J.,Brighton Crop Protection Conference-Weeds,1993,1,35-41.
52 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,119-120.
53 Lutman P.J.W.,Bowerman P.,Palmer G.M.and Whytock G.P.,Brighton Crop Protection Conference-Weeds,1995,1,243-250.
54 Lutman P.J.W.,Bowerman P.,Palmer G.M.and Whytock G.P.,Brighton Crop Protection Conference-Weeds,1995,1,45-48.
55 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,116-117
56 Costales M.J.,Kleschick W.A.,Her R.J.,Weimer M.R.,1998,US 5763359.
57 Ulrich H.,Herbert G.,Peter G.,DE 3,402,328.
58 张一宾,现代农药,2003,2(4),31-36.
59 顾保权,朱伟清,范文政,钱红,刘建梅,现代农药,2002,6,9-11.
60 程志明,世界农药,2001,23(6),18-23.
61 Okada I.,1988,EP 28987p,CA,110:95234.
62 刘长令,农药,2003,42(10),1-4.
63 张弘,孟铃,农药,2003,42(3),14-17.
64 Heil M.,Bretschneider T.,Militzer H.C.,2000,DE 19,838,708.
65 Ulrich H.,Herbert G.,Peter G.,2001,DE 19,961,330.
66 Elbe H.L.,Rieck H.,Dunkel R.,Wachendorfe,N.,U.,Mauler M.A.,Kuck,K.H.,Kugler,M.,Jaetsch,T.,2002,WO 0208,195.
67 Elbe H.L.,Rieck H.,Dunkel R.,Wachendorfe N.U.,Mauler M.A.,Kuck,K.H.,Kugler,M.,Jaetsch,T.,2003,WO 0310,149,CA,138:137308u.
68 周春隆,酸性染料及酸性媒介染料,北京,化学工业出版社.1989,102.
69 张伟,赵德丰,Freeman H.S.,染料与染色,2004,41(2),81-83.
70 BASF Corporation,Ger.Offen.2,843,873
71 刘深,大连理工大学博士学位论文,2006,2-3.
72 Knott L.,Ber.,1883,16,257.
73 Yadav J.S.,Reddy B.V.S.,Satheesh G.,P.Lakshmi N.,Kumar S.K.and Kunwar A.C.,Tetrahedron Lett.,2004,45,8587-8590.
74 L(?)vai A.,Silva A.M.S.,Pinto D.C.G.A.,Cavaleiro J.A.S.,Alkorta I.,Elguero J.and Jeko|¨ J.,Eur.J.Org.Chem.2004,4672-4679.
75 Chandrasekhar S.,Rajaiah G.and Srihari P.,Tetrahedron Lett.,2001,42,6599-6601.
76 Haddad N.,Salvagno A.and Busacca C.,Tetrahedron Lett.,2004,45,5935-5937
77 Meesala R.and Nagarajan R.,Tetrahedron Lett.,2006,47,7557-7561.
78 Rathelot P.,Azas N.,El-Kashef H.,Delmas F.,Giorgio C.D.,David P.T.,Maldonado J.,Vanelle P.,Eur.J.Meal Chem.,2002,37,671-679.
79 Abadi A.H.,Eissa A.A.H.,and Hassan G.S.,Chem.Pharm.Bull.,2003,51(7),838-844.
80 Abdel Moneam M.I.,Monatshefte f(?)r Chemie,2004,135,45-53.
81 Sridhar R.and Perumal P.T.,Tetrahedron,2005,61,2465-2470.
82 Lee K.Y.,Kim J.M.and Kim J.N.,Tetrahedron Lett.,2003,44,6737-6740.
83 Peruncheralathan S.,Yadav A.K.,Ila H.,and Junjappa H.,J.Org.Chem.2005,70,9644-9647.
84 Dodd D.S.and Martinezb R.L.,Tetrahedron Lett.,2004,45,4265-4267.
85 Xie F.,Cheng G.,and Hu Y.,J.Comb.Chem.2006,8,286-288.
86.Wang Jian-Ping,Fu Yong-Ju,Wamg Jian-Ge,Chemical Research and Application,2007,19(12),1379-1381.
87.Campbell,Simon F.;Cross,Peter E.;Stubbs,John K.,1986,US 4,572,909.
88.Georges A,I1 Farmaco;edizione scientifica,1973,28(4),323-50.
89.Igarashi Takeshi;Morisaki Hirobumi;Goto Nobuichi.Microbiology and immunology,2004,48(3),155-62.
90.Kankan,Rajendra Narayanrao;Rao,Dharmaraj Ramachandra;Srinivas,Pathi L.,2004 WO 2004063188.
91.Tang Qinghu;Wang Ye;Liang Jun;Wang Ping;Zhang Qinghong;Wan Huilin,Chemical communications(Cambridge,England),2004,(4),440-1.
92.Konakanchi Durga.,2001,US 6,303,787.
93.Shuttleworth J;Morser J;Burke D.C.,European journal of biochemistry,1983,133(2),399-404.
94.Moon,Young-Ho;Lee,Kyung-Ik;Lee,Gwan-Sun.,2002,US 6,423,846.
95.Haider Z;Bano K.A.,The Journal of the Pakistan Medical Association,1984,34(1),13-6.
96.Avrutov,Ilya;Mendelovici,Marioara.,2002,WO 2002062786.
97.Sendi P;Gafni A;Birch S.,Health economics,2002,11(1),23-31.
98.Broeckx,Rudy Laurent Maria;De Smaele,Dirk;Leurs,Stefan Marcel Herman.,2003,WO 2003008406.
99.Krakowka Steven;Ellis John A;McNeilly Francis;Gilpin Diedre;Meehan Brian;McCullough Ken;Allan Gordon.,Viral immunology,2002,15(4),567-82.
100.Stampa,Alberto;Camps,Pelayo;Rodriguez,Gloria;Bosch,Jordi;Onrubia,Mariadel Carmen,2000,US 6,084,100.
101.Vinogradov A V;Arutiunov G P;Gel'fand I N;Glazunov A S;Zhuravleva A I,Laboratornoe delo,1984,(12),717-9.
102.S.M.McElvain,M.A.Goese.J.Am.Chem.Soc.1941,63,2283-2285.
103.Gerard R.Kieczykowski,Ronald B.Jobson,David G.Melillo,Donald.F.Reinhold,Victor J.Grenda,Ichiro Shinkai.J.Org.Chem,1995,60(25),8310-8315.
104.Julian M.W.,Christopher R.,Gary A.,Jared C.,Zev S.,Ryan M.,Timothy C.H.,Simon L.,Robert G.J.Med.Chem.,2004,47(1),175-187.
105.Verhoff,Frank H.;Snow,Robert A.;Pace,Gary W,2001,WO 2001085345.
106.Chan,Pak;Heatherly,Kathy;Kupiec,Thomas C.;Trissel,Lawrence A.International Journal of Pharmaceutical Compounding,2005,12(3),276-278.
107.Zimmerer,Rupert O.;Pipkin,James D.;Thompson,Diane O.;Mosher,Gerold L.,2005,WO 2005065651.
108.张伟,钟武,李松,国际药学研究杂志,2007,34(5),341-345.
109.慕长炜,覃兆海,现代农药,2003,2(2),1-6.
110.张永庆,赵关娟,王瑞琴,杨月萍,崔灵,宁夏农林科技,2008,5,35-37.
111.郭良芝,邱学林,郭青云,辛存岳,魏有海,翁华,农药,2004,43(3),140-141.
112.周曙光,詹波,李丽娟,杭州化工,2006,36(2),8-10.
113.王广成,吴春先,高立明,陈丙坤,农药,2007,46(12),834-836.
114.Boger,D.L;Panek,J.S.;Meier,M.M.J.Org.Chem.1982,47,895.
115.Stanforth,S.P.;Tarbit,B.;Watson,M.D.Tetrahedron Lett.2003,44,693.
116.Marta Altuna-Urquijo,Alexander Gehre,Stephen P.Stanforth a,Brian Tarbit Tetrahedron,2009,65,975-984.
117.(a) Hantzsch,A.Ann.1882,215,1.
(b) Raboin,J.-C.;Kirsch,G.;Beley,M.J.Heterocycl.Chem.2000,37,1077.
118.陆绍荣,化学研究,2003,14(2),50-52.119.
119.Dondoni,A.,Massi,A.,Minghini,E.J.Org.Chem.2003,68,6172-6183.
120.Kro|¨hnde,F.Synthesis 1976,1.(Review).
121.Malkov,A.V,;Bella,M.;Stara,I.G.;Kocovsky,P.Tetrahedron Lett.2001,42,3045.
122.(a) Mohammad M,Al-Arab,J.Heterocycl.Chem.1989,26,1665.
(b) Pedro Victory,Jos(?) I,Borrell,Anton Vidal-Ferran,Tetrahedron Lett,1991,32(39),5375.
123.Jes(?)s A,Varela,Carlos Sa(?).Synlett,2008,2571-2578.
124.Gao,Y.;Shi,D.Q.;Zhou,L.H.;Dai,G.Y.J..Org.Chem(Ch).1996,16,548.
125.Melot,J.M.;Boullet,F.M.;Foucaud,A.Tetrahedron Lett.1986,27,493.
126.Yamawaki,J.;Kawate,T.;Ando,T.;Hanafusa,T.Bull.Chem.Soc.Jpn.1983,56,1885.
127.Boullet,F.M.;Villemin,D.;Ricard,M.;Moison,A.;Foucaud,A.Tetrahedron.1985,41,1259.
128.Yamawaki,J.;Yamawaki,J.;Kawate,T.;Sumi,S.;Hanafusa,T.Bull.Chem.Soc.Jpn.1982,55,2504;
129.Yamawaki,J.;Ando,T.;Hanafusa,T.Chem.Lett.1981,(8),1143;
130.Villemin,D.J.Chem.Soc.,Chem.Commun.1985,(13),870.
131.Roberto Ballinia,and Alessandro Palmieria.Adv.Synth.Catal.2006,348,1154 - 1156.
132.Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J..Org.Chem(Ch).2002,22,909;
133.Wang,X.S.;Shi,D.Q.;Tu,S.J.Synth.Commun.2003,33,119;
134.Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Org.Chem(Ch) 2003,23,210;
135.Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Chem.2003,21,1114;
136.Wang,X.S.;Shi,D.Q.;Yu,H.Z.;Wang,G.F.;Tu,S.J.Synth.Commun.2004,34,509.
137.Rosenthal,D.;Braundrup,G.;Davis,K.H.;Wall,M.E.J.Org.Chem.1965,30,3689.
138.Bull,S.D.;Davies,S.G.;Delgado-Ballester,S.;Fenton,G.;Kelly,P.M.;Smith,A.D.Synlett 2000,1257.
139.Miller,K.J.;Kitagawa,T.T.;Abu-Omar,M.M.Organometallics 2001,20,4403.
140.Lei Yang,Li-Wen Xu and Chun-Gu Xia,Tetrahedron Letters,2005,46,3279-3282.
141.F.Matloubi Moghaddam,G.Rezanejade Bardajee,and R.Oftadeh Chadomeshine Veranlou Synthetic Communications,2005,35(18),2427-2433.
142.Xiang-shan Wang,Zhao-sen Zeng,Da-qing Shi,Xian-yong Wei,and Zhi-min Zong,Synthetic Communications,2004,34(23),4331-4338.
143.Abdolkarim Zare,Alireza Hasaninejad,Mohammad Hassan,Beyzavi,Ahmad Reza Moosavi Zare,Ali Khalafi-Nezhad,Fatemeh Asadi,Leila Baramaki,Sedigheh Jomhori-Angali,and Rokhsareh Ghaleh-Golabil,Synthetic Communications,2009,39,139-157.
1 Japan Patent Application No.63-107949(1987).
2 US Patent No.4742063(1987).
3 US Patent No.4866064(1989).
4 Suiko,I.;Hayashida,S.and Nakatsu,S.Agric.Biol.Chem.,1982,46(11),2691-2695.
5 Abdou,N.A.;Soliman,S.N.;Abou Sier,A.H.Bull Fac Pharm.,1990,28(2),29
6 Cooper,K.;Steele,J.;Richardson,K.EP 329357
7 Consejo Superior De Investigaciones Cientificals,Span.Pat.460443(1979)
8 U.S.Pat.3948885(C.A.1976,85:6010).
9 Liri,O.;Ferrarini,P.L.;Tontti,I.P.Farmaco Ed.Sci.,1976,31,797.
10(a)Alvarez,R;Velazquez,S.;San-Felix,A.et al.J.Med.Chem.,1994,37,4185.;
(b) De Clercq,E.Medicinal Research Reviews,2002,22(6),531.
11.Kohn,E.C.;Liotta,L.A.US Patent 637,145(1991).
12.Gemma L.Thomas,Richard J.Spandl,Freija G.Glansdorp,Martin Welch,Andreas Bender,Joshua Cockfield,Jodi A.Lindsay,Clare Bryant,Derek F.J.Brown,Olivier Loiseleur,Angew.Chem.Int.Ed.2008,47,2808 -2812.
13.Yakenaka,K.;Tsuji,T.J.Heterocyclic Chem.,1996,33,1367.
14.Busch,B.;Johnson,A.T.;Martin,R.;Mohan,R.;Stevens,W.C.WO 2005072731,2005.
15.Santagati,A.;Santagati,M.;Russo,F.;Ronsisvalle,G.J.Heterocyclic Chem.,1988,25,949.
16.Tsuji,T.J.Heterocyclic Chem.,1991,28,489.
17.Kohn,E.C.;Liotta,L.A.;U.S.Pat.Appl.US 637,145(CA.115:248099).
18.Pavitra Kumar Dutt;J.Chem.Soc.,1921,199,2088.
19.Oulin,F.Helv.Chim.Acta.,1952,35,167.
20.崔蕾,陈家胜,刘方明,解正峰,孙亚栋,王厚勇;有机化学,2006,26,963-966
21.Okabe,T.;Mackawa,K.and Taniguchi,E.Agr.Biol.Chem,1973,37,1197.
1.Dong,H.S.,Wei,K.,Wang,Q.L.,Quan,B.J.Chin.Chem.Soc.,2000,47,343-346.
2.Ranatunge R.R.,Augustyniak M.,Bandarage U.K.,Earl R.A.,Ellis J.L.,Garvey D.S.,Janero D.R.,Letts L.G.,Martino A.M.,Murty M.G.,Richardson S.K.,Schroeder J.D.,Shumway M.J.,Tam S.W.,Trocha A.M.,and Young D.V.,J.Med.Chem.,2004,47,2180-2193.
3.Chimenti F.,Fioravanti R.,Bolasco A.,Manna F.,Chimenti P.,Secci D.,Befani O.,Turini P.,Ortuso F.,and Alcaro S.,J.Med.Chem.2007,50,425-428.
4.Chimenti F.,Bolasco A.,Manna F.,Secci D.,Chimenti P.,Befani O.,Turini P.,Giovannini V.,Mondovi B.,Cirilli R.,and La Torre F.,J.Med.Chem.2004,47,2071-2074.
5.Chimenti F.,Maccioni E.,Secci D.,Bolasco A.,Chimenti P.,Granese A.,Befani O.,Turini P.,Alcaro S.,Ortuso F.,Cirilli R.,La Torre F.,Cardia M.C.,and Distinto S.,J.Med.Chem.2005,48,7113-7122.
6.Kees K.L.,Fitzgerald J.J.,Jr.,Steiner K.E.,Mattes J.F.,Mihan B.,Tosi T.,Mondoro D.,and McCalebr M.L.,J.Med.Chem.1996,39,3920-3928.
7.Tanitame A.,Oyamada Y.,Ofuji K.,Fujimoto M.,Iwai N.,Hiyama Y.,Suzuki K.,Ito H.,Terauchi H.,Kawasaki M.,Nagai K.,Wachi M.,and Yamagishi J.,J.Med.Chem.2004,47,3693-3696.
8.Pinto D.J.P.,Orwat M.J.,Wang S.,Fevig J.M.,Quan M.L.,Amparo E.,Cacciola J.,Rossi K.A.,Alexander R.S.,Smallwood A.M.,Luettgen J.M.,Liang L.,Aungst B.J.,Wright M.R.,Knabb R.M.,Wong P.C.,Wexler R.R.,and Lain P.Y.S.,J.Med.Chem.2001,44,566-578.
9.Boyd D.B.,Morin R.B.,Gorman M.,Theoretical and Physicochemical Studies on b-Lactam Antibiotics in b-Lactam Antibiotics,Chemistry and Biology(1),Academic Press,New York,1982,437-545.
10.Pattenden,G.,J.Heterocycl.Chem.,1992,29,607-618.
11.Turan-Zitouni G.,Chevallet P.,Kilic F.S.,Erol K.,Eur.J.Med.Chem.,2000,35,635-641.
12.O|¨zdemir A.,Turan-Zitouni G.,Kaplancikl Z.A.,Revial G.,Gu|¨ven K.,Eur.J.Med.Chem.,2007,42,403-409.
13.Sawhney S.N.,Bhutani S.and Vir D.,Indian J Chemistry,1989,28B,667-672.
14.Drake,N.L.,Allen,P.,Org.Synth.Collect.J.Wiley and Sons,Inc.,London,1948,1,77-78.;Kohler,E.P.,Chadwell,H.M.,Org.Synth.Collect.J.Wiley and Sons,Inc.,London,1948,1,78-79.
15.Chimenti F.,Maccioni E.,Secci D.,Bolasco A.,Chimenti P.,Granese A.,Befani O.,Turini P.,Alcaro S.,Ortuso F.,Cirilli R.,La Torre F.,Cardia M.C.,and Distinto S.,J.Med.Chem.2005,48,7113-7122.
1.Davis L.,Olsen G.E.,Klein J.T.,Kapples K.J.,Huger F.P.,Smith C.P.,Petko W.W.,Cornmfeldt M.,and Effland R.C.,J.Med.Chem.1996,39,582-587.
2.Vacher B.,Bonnaud B.,Funes P.,Jubault N.,Koek W.,Assie M.B.,and Cosi C.,J.Med.Chem.1998,41,5070-5083.
3.Gezginci M.H.,Martin A.R.,and Franzblau S.G.,J.Med.Chem.2001,44,1560-1563.
4.Shan R.,Howlett S.E.,and Knaus E.E.,J.Med.Chem.2002,45,955-961.
5.Choong,I.C.,Lew,W,,Lee,D.,Pham,P.,Burdett,M.T.,Lam,J.W.,Wiesmann,C.,Luong,T.N.,Fahr,B.,DeLano,W.L.,McDowell,R.S.,Allen,D.A.,Erlanson,D.A.,Gordon,E.M.,O'Brien,T.,J.Med.Chem.2002,45,5005-5022.
6.Cosford N.D.P.,Tehrani L.,Roppe J.,Schweiger E.,Smith N.D.,Anderson J.,Bristow L.,Brodkin J.,Jiang X.H.,McDonald I.,Ran S.,Washburn M.,and Varney M.A.,J.Med.Chem.2003,46,204-206.
7.Shao B.,Victory S.,Ilyin V.I.,Goehring R.R.,Sun Q.,Hogenkamp D.,Hodges D.D.,Islam K.,Sha D.,Zhang C.,Nguyen P.,Robledo S.,Sakellaropoulos G.,and Carter R.B.,J..Med.Chem.2004,47,4277-4285.
8.Wei Z.L.,Xiao Y.,Yuan H.,Baydyuk M.,Petukhov P.A.,Musachio J.L.,Kellar K.J.,and Kozikowski A.P.,J.Med.Chem.2005,48,1721-1724.
9.Zhao H.,Serby M.D.,Xin Z.,Szczepankiewicz B.G.,Liu M.,Kosogof C.,Liu B.,Nelson L.T.J.,Johnson E.F.,Wang S.,Pederson T.,Gum R.J.,Clampit J.E.,Haasch D.L.,Abad-Zapatero C.,Fry E.H.,Rondinone C.,Trevillyan J.M.,Sham H.L.,and Liu G.,J.Med.Chem.2006,49,4455-4458.
10.Bemis,G.,Murcko,M.A.,J.Med.Chem.1996,39,2887.
11.Kohn,E.C.,Liotta,L.A.,US 637145(Chem Abstr:1991,115,248099)
12.Dong,H.S.,Wei,K.,Wang,Q.L.,Quan,B.J.Chin.Chem.Soc.2000,47,343-346.
13.Pedro Victory,Jos(?) I.Borrell,Anton Vidal-Ferran.Tetrahedron Lett.2001,31(22),3497-3505.
14.Mohammad M,Al-Arab.J.Heterocycllic.Chem.1989,26,1665.
1.Utimoto,K.;Obayashi,M.;Shishiyama,Y.;Inoue,M.;Nozaki,H.Tetrahedron Lett.1980,21,3389-3392.
2.Nagata,W.;Yoshioka,M.Org.React.1977,25,255,and the references cited therein.
3.Utimoto,K.;Wakabayashi,Y.;Horie,T.;Inoue,M.;Shishiyama,Y.;Obayashi,M.;Nozaki,H.Tetrahedron 1983,39,967-973.
4.Aurore Louder,Rakeshwar Bandichhor,Liangxing Wu,Kevin Burgess.Tetrahedron.2008 64,3642e3654.
5.Davis,Edward Mark;Ellis,James E.1998,WO 9815524.
6.Katsuhiko Hino,Yasutaka Nagai,Hitoshi Uno,Yoshinobu Masuda,Makoto Oka,Tadahiko Karasawa.J.Med.chem.1988,31,107-117.
7.Ciller,J.A.,Martin,N.,Quinteiro,M.,Seoane,C.,Soto,J.L.Organic preparations and procedures international.1986,18(4),227-36.
8.Salem,Mownir A.I.;Madlour,Hassan M.F.;Soliman,E1-Sayed A.;Mahmoud;Naglaa F.H.Heterocycles,2000,53(5),1129-1143.
9.Gao,Y.;Shi,D.Q.;Zhou,L.H.;Dai,G.Y.J.Org.Chem(Ch).1996,16,548.
10.Melot,J.M.;Boullet,F.M.;Foucaud,A.Tetrahedron Lett.1986,27,493.
11.Yamawaki,J.;Kawate,T.;Ando,T.;Hanafusa,T.Bull,Chem.Soc.Jpn.1983,56,1885.
12.Boullet,F.M,;Villemin,D.;Ricard,M.;Moison,A.;Foucaud,A.Tetrahedron 1985,41,1259.
13.(a) Yamawaki,J.;Yamawaki,J.;Kawate,T.;Sumi,S.;Hanafusa,T.Bull.Chem.Soc.Jpn 1982,55,2504;
(b) Yamawaki,J.;Ando,T.;Hanafusa,T.Chem.Lett.1981,(8),1143;
(c) Villemin,D.J.Chem.Soc.,Chem.Commun.1985,(13),870.
14.Roberto Ballinia,and Alessandro Palmieria.Adv.Synth.Catal.2006,348,1154 - 1156.
15.(a) Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Org.Chem(Ch).2002,22,909;
(b) Wang,X.S.;Shi,D.Q.;Tu,S.J.Synth.Commun.2003,33,119;
(c) Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Org.Chem(Ch) 2003,23,210;
(d) Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Chem.2003,21,1114;
(e) Wang,X.S.;Shi,D.Q.;Yu,H.Z.;Wang,G.F.;Tu,S.J.Synth.Commun.2004,34,509.
2 US Patent No.4742063(1987).
3 US Patent No.4866064(1989).
4 Suiko,I.;Hayashida,S.and Nakatsu,S.Agric.Biol.Chem.,1982,46(11),2691-2695.
5 Okabe,T.;Maekawa,K.and Taniguchi,E.Agric.Biol.Chem.,1973,37,1197.
6 Tsuji,T.and Ueda,T.Chem.Pharm.Bull.,1974,22,471.
7 Tsuji,T.and Otsuka,Y.Heterocycles,1980,14,197.
8 Okabe,T.;Taniguchi,E.and K.Maekawa,Bull.Chem.Soc.Jpn.,1974,47,2813.
9 Okabe,T.;Mackawa,K.and Taniguchi,E.Agr.Biol.Chem,1973,37,1197.
10 Tsuji,T.and Takenaka,K.Bull.Chem.Soc.Japan,1982,55,637-638.
11 Takenaka,K.and Tsuji,T.J.Heterocyclic Chem,1996,33,1367-1370.
12 Gabriel,K.;Marks,P.J.and Constance,G.C,J.Org.Chem.,1980,45(24),4680-4683.
13 Shafiee,A.and Lalezari,I.,J.Heterocyclic.Chem.,1975,12,675.
14 Kuderna J.G.;Skiles,R.D.and Pilgram,K.,J.Org.Chem.,1971,36,3506.
15 Doad,G..J.;Okor,D.I.and Scheinmann,F.J.Chem.Soc.Perkin Trans1,1988,2933.
16 Lauer,R.F.and Zenchoff,G.J.Heterocyclic.Chem.,1976,13,291.
17 Kornis,G..Marks,P.J.and Chidester,C.G.,J.Org.Chem.,1980,45,4860-4863.
18 European Patent Application No.87103967.3(1987).
19 Salimov,T.M.;Kukaniev,M.A.;Sattorov,I.T.and Osimov,D.M.Pharma Chem J 2005,39,6,311-312.
20 Saifidin,Safarov.;Muhamacho,A.Kukaniev,:Elena,Karpuk and Herbert,Meier,J.Heterocycl.Chem 2007,44,269-271.
21 Katritzky,A.R.,Rees,C.W.,Scriven,E.F.V.,Elguero J.,Comprehensive Heterocyclic Chemistry,Pergamon,Oxford,1996,3,1-75.
22 Cottineau,B.,Toto,P.,Marot,C.,Pipaud,A.,Chenault,J.,Bioorg.Med.Chem.Lett.2002,12,2105-2108.
23 Lee,K.Y.,Kim,J.M.,Kim,J.N.,Tetrahedron Lett.2003,44,6737-6740.
24 Ranatunge R.R.,Earl R.A.,Garvey D.S.,Janero D.R.,Gordon L.L.,Allison M.M.,Murty M.G.,Richardson S.K.,Schwalb D.J.,Young D.V.and Zemtseva I.S.,Bioorg. Med.Chem.Lett., 2004,14,6049-6052
25 Ranatunge R.R., Augustyniak M., Bandarage U.K., Earl R.A., Ellis J.L., Garvey D.S.,Janero D.R., Letts L.G., Martino A.M., Murty M.G., Richardson S.K., Schroeder J.D.,Shumway M.J., William S.T., Trocha A.M., and Young D.V., J.Med.Chem.2004,47,2180-2193.
26 Feldmann, M.B., Fionula M., Maini, R.N., Annu.Rev.Immunol.1996,14, 397-440.
27 Regan J., Breitfelder S., Cirillo P., Gilmore T., Graham A.G., Hickey E., Klaus B.,Madwed J., Moriak M., Moss N., Pargellis C, Pav S., Proto A., Swinamer A., Tong L., and Torcellini C, J.Med.Chem.2002,45, 2994-3008.
28 Regan J., Capolino A., Cirillo P.F., Gilmore T., Graham A.G., Hickey E., Kroe R.R.,Madwed J., Moriak M., Nelson R., Pargellis C.A., Swinamer A., Torcellini C, Tsang M.,and Moss N., J.Med.Chem.2003,46, 4676-4686.
29 Goldstein D.M., Alfredson T., Bertrand J., Browner M.F., Clifford K., Dalrymple S.A.,Dunn J., Moar J.F., Harris S., Labadie S.S., Fargue J.L., Lapierre J.M., Larrabee S., Li F., Papp E., WeeneyD.M., Ramesha C, Roberts R., Rotstein D., Pablo B.S., Sjogren E.B., So O.Y., Talamas F.X., Tao W., Trejo A., Villasenor A., Welch M., Welch T., Weller P., Whiteley P.E., Young K., and Zipfel S., J.Med.Chem.2006,49, 1562-1575.
30 Tanitame A., Oyamada Y., Ofuji K., Fujimoto M., Iwai N., Hiyama Y., Suzuki K., Ito H., Terauchi H., Kawasaki M., Nagai K., Wachi M., and Yamagishi J., J.Med.Chem.2004,47, 3693-3696.
31 Wei F., Zhao B.X., Huang B., Zhang L., Sun C.H., Dong W.L., Shin D.S.and Miao J.Y., Bioorg.Med.Chem.Lett.2006,16, 6342-6347.
32 Ho C.Y., Ludovici D.W., Maharoof U.S.M., Mei J., Sechler J.L., Tuman R.W., Strobel E.D., Andraka L., Yen H.K., Leo G., Li J, Almond H., Lu H., DeVine A., Tominovich R.M., Baker J., Emanuel S., Gruninger R.H., Middleton S.A., Johnson D.L., and Galemmo R.A., Jr., J.Med.Chem.2005,48, 8163-8173.
33 Pinto D.J.P., Orwat M.J., Wang S., Fevig J.M., Quan M.L., Amparo E., Cacciola J.,Rossi K.A., Alexander R.S., Smallwood A.M., Luettgen J.M., Liang L., Aungst B.J.,Wright M.R., Knabb R.M., Wong P.C, Wexler R.R., and Lam P.Y.S., J.Med.Chem.2001,44, 566-578.
34 Pruitt J.R.,Pinto D.J.P.,Galemmo R.A.,Jr.,Alexander R.S.,Rossi K.A.,Wells B.L.,Drummond S.,Bostrom L.L.,Burdick D.,Bruckner R.,Chen H.,Smallwood A.,Wong P.C.,Wright M.R.,Bai S.,Luettgen J.M.,Knabb R.M.,Lam P.Y.S.,and Wexler R.R.,J.Med.Chem.2003,46,5298-5315.
35 Jia,Z.J.,Wu,Y.,Huang,W.,Zhang,P.,Song,Y.,Woolfrey,J.,Sinha,U.,Arfsten,A.E.,Edwards,S.T.,Hutchaleelaha,A.,Hollennbach,S.J.,Lambing,J.L.,Scarborough,R.M.,Zhu,B.Y.Bioorg.Med.Chem.Lett.,2004,14,1229-1234.
36 Thompson H.A.,Swanson C.P.and Norman A.G.,Gazz,107:476(1946)[C.A.,41,3774;(1947)].
37 George L.M.,Norman K.S.,Phytopathology,1949,39,721-751.CA,44:781h
38 Norman K.S.,US 2510724,1950,CA,44:8375h
39 Gysin H.and Margot A.US Patent 2,754,244(1956).
40 Shigematsbl M.,EP 355,409(1989),CA,112:139041p
41 Yoshiaki K,Japan pesticide Information,1988,53,27-31.
42 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,57-60.
43 Tomlin C.D.S.,The Pesticide Manual(12th ed.),British Crop Council,Surrey,UK,2000,795.
44 Ikeda K.,Sugaya K.,Coh A.,Chemical Regulation of Plants,1986,21(2),152-163.
45 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,41-43.
46 Kogyok Y.K.,JP 57-38,705,CA,97:51218n.
47 Takao K.,1980,JP 35035,CA,93,20 750t.
48 Takao K.,1980,JP 35038,CA,93,20 752v.
49 Tice C.M.,Musco V.A.,Roemmele,R.C.,Warner,H.L.,1995,US 5,453,414.
50 Hartfiel,U.,Dorfmeister,G.,Frake,H.,Geisler,J.,Johann,G.,Rees,R.,1993,US 5,405,829.
51 Marks M.J.,Brighton Crop Protection Conference-Weeds,1993,1,35-41.
52 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,119-120.
53 Lutman P.J.W.,Bowerman P.,Palmer G.M.and Whytock G.P.,Brighton Crop Protection Conference-Weeds,1995,1,243-250.
54 Lutman P.J.W.,Bowerman P.,Palmer G.M.and Whytock G.P.,Brighton Crop Protection Conference-Weeds,1995,1,45-48.
55 刘长令主编,世界农药大全-除草卷,化学工业出版社(北京),2002,8,116-117
56 Costales M.J.,Kleschick W.A.,Her R.J.,Weimer M.R.,1998,US 5763359.
57 Ulrich H.,Herbert G.,Peter G.,DE 3,402,328.
58 张一宾,现代农药,2003,2(4),31-36.
59 顾保权,朱伟清,范文政,钱红,刘建梅,现代农药,2002,6,9-11.
60 程志明,世界农药,2001,23(6),18-23.
61 Okada I.,1988,EP 28987p,CA,110:95234.
62 刘长令,农药,2003,42(10),1-4.
63 张弘,孟铃,农药,2003,42(3),14-17.
64 Heil M.,Bretschneider T.,Militzer H.C.,2000,DE 19,838,708.
65 Ulrich H.,Herbert G.,Peter G.,2001,DE 19,961,330.
66 Elbe H.L.,Rieck H.,Dunkel R.,Wachendorfe,N.,U.,Mauler M.A.,Kuck,K.H.,Kugler,M.,Jaetsch,T.,2002,WO 0208,195.
67 Elbe H.L.,Rieck H.,Dunkel R.,Wachendorfe N.U.,Mauler M.A.,Kuck,K.H.,Kugler,M.,Jaetsch,T.,2003,WO 0310,149,CA,138:137308u.
68 周春隆,酸性染料及酸性媒介染料,北京,化学工业出版社.1989,102.
69 张伟,赵德丰,Freeman H.S.,染料与染色,2004,41(2),81-83.
70 BASF Corporation,Ger.Offen.2,843,873
71 刘深,大连理工大学博士学位论文,2006,2-3.
72 Knott L.,Ber.,1883,16,257.
73 Yadav J.S.,Reddy B.V.S.,Satheesh G.,P.Lakshmi N.,Kumar S.K.and Kunwar A.C.,Tetrahedron Lett.,2004,45,8587-8590.
74 L(?)vai A.,Silva A.M.S.,Pinto D.C.G.A.,Cavaleiro J.A.S.,Alkorta I.,Elguero J.and Jeko|¨ J.,Eur.J.Org.Chem.2004,4672-4679.
75 Chandrasekhar S.,Rajaiah G.and Srihari P.,Tetrahedron Lett.,2001,42,6599-6601.
76 Haddad N.,Salvagno A.and Busacca C.,Tetrahedron Lett.,2004,45,5935-5937
77 Meesala R.and Nagarajan R.,Tetrahedron Lett.,2006,47,7557-7561.
78 Rathelot P.,Azas N.,El-Kashef H.,Delmas F.,Giorgio C.D.,David P.T.,Maldonado J.,Vanelle P.,Eur.J.Meal Chem.,2002,37,671-679.
79 Abadi A.H.,Eissa A.A.H.,and Hassan G.S.,Chem.Pharm.Bull.,2003,51(7),838-844.
80 Abdel Moneam M.I.,Monatshefte f(?)r Chemie,2004,135,45-53.
81 Sridhar R.and Perumal P.T.,Tetrahedron,2005,61,2465-2470.
82 Lee K.Y.,Kim J.M.and Kim J.N.,Tetrahedron Lett.,2003,44,6737-6740.
83 Peruncheralathan S.,Yadav A.K.,Ila H.,and Junjappa H.,J.Org.Chem.2005,70,9644-9647.
84 Dodd D.S.and Martinezb R.L.,Tetrahedron Lett.,2004,45,4265-4267.
85 Xie F.,Cheng G.,and Hu Y.,J.Comb.Chem.2006,8,286-288.
86.Wang Jian-Ping,Fu Yong-Ju,Wamg Jian-Ge,Chemical Research and Application,2007,19(12),1379-1381.
87.Campbell,Simon F.;Cross,Peter E.;Stubbs,John K.,1986,US 4,572,909.
88.Georges A,I1 Farmaco;edizione scientifica,1973,28(4),323-50.
89.Igarashi Takeshi;Morisaki Hirobumi;Goto Nobuichi.Microbiology and immunology,2004,48(3),155-62.
90.Kankan,Rajendra Narayanrao;Rao,Dharmaraj Ramachandra;Srinivas,Pathi L.,2004 WO 2004063188.
91.Tang Qinghu;Wang Ye;Liang Jun;Wang Ping;Zhang Qinghong;Wan Huilin,Chemical communications(Cambridge,England),2004,(4),440-1.
92.Konakanchi Durga.,2001,US 6,303,787.
93.Shuttleworth J;Morser J;Burke D.C.,European journal of biochemistry,1983,133(2),399-404.
94.Moon,Young-Ho;Lee,Kyung-Ik;Lee,Gwan-Sun.,2002,US 6,423,846.
95.Haider Z;Bano K.A.,The Journal of the Pakistan Medical Association,1984,34(1),13-6.
96.Avrutov,Ilya;Mendelovici,Marioara.,2002,WO 2002062786.
97.Sendi P;Gafni A;Birch S.,Health economics,2002,11(1),23-31.
98.Broeckx,Rudy Laurent Maria;De Smaele,Dirk;Leurs,Stefan Marcel Herman.,2003,WO 2003008406.
99.Krakowka Steven;Ellis John A;McNeilly Francis;Gilpin Diedre;Meehan Brian;McCullough Ken;Allan Gordon.,Viral immunology,2002,15(4),567-82.
100.Stampa,Alberto;Camps,Pelayo;Rodriguez,Gloria;Bosch,Jordi;Onrubia,Mariadel Carmen,2000,US 6,084,100.
101.Vinogradov A V;Arutiunov G P;Gel'fand I N;Glazunov A S;Zhuravleva A I,Laboratornoe delo,1984,(12),717-9.
102.S.M.McElvain,M.A.Goese.J.Am.Chem.Soc.1941,63,2283-2285.
103.Gerard R.Kieczykowski,Ronald B.Jobson,David G.Melillo,Donald.F.Reinhold,Victor J.Grenda,Ichiro Shinkai.J.Org.Chem,1995,60(25),8310-8315.
104.Julian M.W.,Christopher R.,Gary A.,Jared C.,Zev S.,Ryan M.,Timothy C.H.,Simon L.,Robert G.J.Med.Chem.,2004,47(1),175-187.
105.Verhoff,Frank H.;Snow,Robert A.;Pace,Gary W,2001,WO 2001085345.
106.Chan,Pak;Heatherly,Kathy;Kupiec,Thomas C.;Trissel,Lawrence A.International Journal of Pharmaceutical Compounding,2005,12(3),276-278.
107.Zimmerer,Rupert O.;Pipkin,James D.;Thompson,Diane O.;Mosher,Gerold L.,2005,WO 2005065651.
108.张伟,钟武,李松,国际药学研究杂志,2007,34(5),341-345.
109.慕长炜,覃兆海,现代农药,2003,2(2),1-6.
110.张永庆,赵关娟,王瑞琴,杨月萍,崔灵,宁夏农林科技,2008,5,35-37.
111.郭良芝,邱学林,郭青云,辛存岳,魏有海,翁华,农药,2004,43(3),140-141.
112.周曙光,詹波,李丽娟,杭州化工,2006,36(2),8-10.
113.王广成,吴春先,高立明,陈丙坤,农药,2007,46(12),834-836.
114.Boger,D.L;Panek,J.S.;Meier,M.M.J.Org.Chem.1982,47,895.
115.Stanforth,S.P.;Tarbit,B.;Watson,M.D.Tetrahedron Lett.2003,44,693.
116.Marta Altuna-Urquijo,Alexander Gehre,Stephen P.Stanforth a,Brian Tarbit Tetrahedron,2009,65,975-984.
117.(a) Hantzsch,A.Ann.1882,215,1.
(b) Raboin,J.-C.;Kirsch,G.;Beley,M.J.Heterocycl.Chem.2000,37,1077.
118.陆绍荣,化学研究,2003,14(2),50-52.119.
119.Dondoni,A.,Massi,A.,Minghini,E.J.Org.Chem.2003,68,6172-6183.
120.Kro|¨hnde,F.Synthesis 1976,1.(Review).
121.Malkov,A.V,;Bella,M.;Stara,I.G.;Kocovsky,P.Tetrahedron Lett.2001,42,3045.
122.(a) Mohammad M,Al-Arab,J.Heterocycl.Chem.1989,26,1665.
(b) Pedro Victory,Jos(?) I,Borrell,Anton Vidal-Ferran,Tetrahedron Lett,1991,32(39),5375.
123.Jes(?)s A,Varela,Carlos Sa(?).Synlett,2008,2571-2578.
124.Gao,Y.;Shi,D.Q.;Zhou,L.H.;Dai,G.Y.J..Org.Chem(Ch).1996,16,548.
125.Melot,J.M.;Boullet,F.M.;Foucaud,A.Tetrahedron Lett.1986,27,493.
126.Yamawaki,J.;Kawate,T.;Ando,T.;Hanafusa,T.Bull.Chem.Soc.Jpn.1983,56,1885.
127.Boullet,F.M.;Villemin,D.;Ricard,M.;Moison,A.;Foucaud,A.Tetrahedron.1985,41,1259.
128.Yamawaki,J.;Yamawaki,J.;Kawate,T.;Sumi,S.;Hanafusa,T.Bull.Chem.Soc.Jpn.1982,55,2504;
129.Yamawaki,J.;Ando,T.;Hanafusa,T.Chem.Lett.1981,(8),1143;
130.Villemin,D.J.Chem.Soc.,Chem.Commun.1985,(13),870.
131.Roberto Ballinia,and Alessandro Palmieria.Adv.Synth.Catal.2006,348,1154 - 1156.
132.Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J..Org.Chem(Ch).2002,22,909;
133.Wang,X.S.;Shi,D.Q.;Tu,S.J.Synth.Commun.2003,33,119;
134.Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Org.Chem(Ch) 2003,23,210;
135.Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Chem.2003,21,1114;
136.Wang,X.S.;Shi,D.Q.;Yu,H.Z.;Wang,G.F.;Tu,S.J.Synth.Commun.2004,34,509.
137.Rosenthal,D.;Braundrup,G.;Davis,K.H.;Wall,M.E.J.Org.Chem.1965,30,3689.
138.Bull,S.D.;Davies,S.G.;Delgado-Ballester,S.;Fenton,G.;Kelly,P.M.;Smith,A.D.Synlett 2000,1257.
139.Miller,K.J.;Kitagawa,T.T.;Abu-Omar,M.M.Organometallics 2001,20,4403.
140.Lei Yang,Li-Wen Xu and Chun-Gu Xia,Tetrahedron Letters,2005,46,3279-3282.
141.F.Matloubi Moghaddam,G.Rezanejade Bardajee,and R.Oftadeh Chadomeshine Veranlou Synthetic Communications,2005,35(18),2427-2433.
142.Xiang-shan Wang,Zhao-sen Zeng,Da-qing Shi,Xian-yong Wei,and Zhi-min Zong,Synthetic Communications,2004,34(23),4331-4338.
143.Abdolkarim Zare,Alireza Hasaninejad,Mohammad Hassan,Beyzavi,Ahmad Reza Moosavi Zare,Ali Khalafi-Nezhad,Fatemeh Asadi,Leila Baramaki,Sedigheh Jomhori-Angali,and Rokhsareh Ghaleh-Golabil,Synthetic Communications,2009,39,139-157.
1 Japan Patent Application No.63-107949(1987).
2 US Patent No.4742063(1987).
3 US Patent No.4866064(1989).
4 Suiko,I.;Hayashida,S.and Nakatsu,S.Agric.Biol.Chem.,1982,46(11),2691-2695.
5 Abdou,N.A.;Soliman,S.N.;Abou Sier,A.H.Bull Fac Pharm.,1990,28(2),29
6 Cooper,K.;Steele,J.;Richardson,K.EP 329357
7 Consejo Superior De Investigaciones Cientificals,Span.Pat.460443(1979)
8 U.S.Pat.3948885(C.A.1976,85:6010).
9 Liri,O.;Ferrarini,P.L.;Tontti,I.P.Farmaco Ed.Sci.,1976,31,797.
10(a)Alvarez,R;Velazquez,S.;San-Felix,A.et al.J.Med.Chem.,1994,37,4185.;
(b) De Clercq,E.Medicinal Research Reviews,2002,22(6),531.
11.Kohn,E.C.;Liotta,L.A.US Patent 637,145(1991).
12.Gemma L.Thomas,Richard J.Spandl,Freija G.Glansdorp,Martin Welch,Andreas Bender,Joshua Cockfield,Jodi A.Lindsay,Clare Bryant,Derek F.J.Brown,Olivier Loiseleur,Angew.Chem.Int.Ed.2008,47,2808 -2812.
13.Yakenaka,K.;Tsuji,T.J.Heterocyclic Chem.,1996,33,1367.
14.Busch,B.;Johnson,A.T.;Martin,R.;Mohan,R.;Stevens,W.C.WO 2005072731,2005.
15.Santagati,A.;Santagati,M.;Russo,F.;Ronsisvalle,G.J.Heterocyclic Chem.,1988,25,949.
16.Tsuji,T.J.Heterocyclic Chem.,1991,28,489.
17.Kohn,E.C.;Liotta,L.A.;U.S.Pat.Appl.US 637,145(CA.115:248099).
18.Pavitra Kumar Dutt;J.Chem.Soc.,1921,199,2088.
19.Oulin,F.Helv.Chim.Acta.,1952,35,167.
20.崔蕾,陈家胜,刘方明,解正峰,孙亚栋,王厚勇;有机化学,2006,26,963-966
21.Okabe,T.;Mackawa,K.and Taniguchi,E.Agr.Biol.Chem,1973,37,1197.
1.Dong,H.S.,Wei,K.,Wang,Q.L.,Quan,B.J.Chin.Chem.Soc.,2000,47,343-346.
2.Ranatunge R.R.,Augustyniak M.,Bandarage U.K.,Earl R.A.,Ellis J.L.,Garvey D.S.,Janero D.R.,Letts L.G.,Martino A.M.,Murty M.G.,Richardson S.K.,Schroeder J.D.,Shumway M.J.,Tam S.W.,Trocha A.M.,and Young D.V.,J.Med.Chem.,2004,47,2180-2193.
3.Chimenti F.,Fioravanti R.,Bolasco A.,Manna F.,Chimenti P.,Secci D.,Befani O.,Turini P.,Ortuso F.,and Alcaro S.,J.Med.Chem.2007,50,425-428.
4.Chimenti F.,Bolasco A.,Manna F.,Secci D.,Chimenti P.,Befani O.,Turini P.,Giovannini V.,Mondovi B.,Cirilli R.,and La Torre F.,J.Med.Chem.2004,47,2071-2074.
5.Chimenti F.,Maccioni E.,Secci D.,Bolasco A.,Chimenti P.,Granese A.,Befani O.,Turini P.,Alcaro S.,Ortuso F.,Cirilli R.,La Torre F.,Cardia M.C.,and Distinto S.,J.Med.Chem.2005,48,7113-7122.
6.Kees K.L.,Fitzgerald J.J.,Jr.,Steiner K.E.,Mattes J.F.,Mihan B.,Tosi T.,Mondoro D.,and McCalebr M.L.,J.Med.Chem.1996,39,3920-3928.
7.Tanitame A.,Oyamada Y.,Ofuji K.,Fujimoto M.,Iwai N.,Hiyama Y.,Suzuki K.,Ito H.,Terauchi H.,Kawasaki M.,Nagai K.,Wachi M.,and Yamagishi J.,J.Med.Chem.2004,47,3693-3696.
8.Pinto D.J.P.,Orwat M.J.,Wang S.,Fevig J.M.,Quan M.L.,Amparo E.,Cacciola J.,Rossi K.A.,Alexander R.S.,Smallwood A.M.,Luettgen J.M.,Liang L.,Aungst B.J.,Wright M.R.,Knabb R.M.,Wong P.C.,Wexler R.R.,and Lain P.Y.S.,J.Med.Chem.2001,44,566-578.
9.Boyd D.B.,Morin R.B.,Gorman M.,Theoretical and Physicochemical Studies on b-Lactam Antibiotics in b-Lactam Antibiotics,Chemistry and Biology(1),Academic Press,New York,1982,437-545.
10.Pattenden,G.,J.Heterocycl.Chem.,1992,29,607-618.
11.Turan-Zitouni G.,Chevallet P.,Kilic F.S.,Erol K.,Eur.J.Med.Chem.,2000,35,635-641.
12.O|¨zdemir A.,Turan-Zitouni G.,Kaplancikl Z.A.,Revial G.,Gu|¨ven K.,Eur.J.Med.Chem.,2007,42,403-409.
13.Sawhney S.N.,Bhutani S.and Vir D.,Indian J Chemistry,1989,28B,667-672.
14.Drake,N.L.,Allen,P.,Org.Synth.Collect.J.Wiley and Sons,Inc.,London,1948,1,77-78.;Kohler,E.P.,Chadwell,H.M.,Org.Synth.Collect.J.Wiley and Sons,Inc.,London,1948,1,78-79.
15.Chimenti F.,Maccioni E.,Secci D.,Bolasco A.,Chimenti P.,Granese A.,Befani O.,Turini P.,Alcaro S.,Ortuso F.,Cirilli R.,La Torre F.,Cardia M.C.,and Distinto S.,J.Med.Chem.2005,48,7113-7122.
1.Davis L.,Olsen G.E.,Klein J.T.,Kapples K.J.,Huger F.P.,Smith C.P.,Petko W.W.,Cornmfeldt M.,and Effland R.C.,J.Med.Chem.1996,39,582-587.
2.Vacher B.,Bonnaud B.,Funes P.,Jubault N.,Koek W.,Assie M.B.,and Cosi C.,J.Med.Chem.1998,41,5070-5083.
3.Gezginci M.H.,Martin A.R.,and Franzblau S.G.,J.Med.Chem.2001,44,1560-1563.
4.Shan R.,Howlett S.E.,and Knaus E.E.,J.Med.Chem.2002,45,955-961.
5.Choong,I.C.,Lew,W,,Lee,D.,Pham,P.,Burdett,M.T.,Lam,J.W.,Wiesmann,C.,Luong,T.N.,Fahr,B.,DeLano,W.L.,McDowell,R.S.,Allen,D.A.,Erlanson,D.A.,Gordon,E.M.,O'Brien,T.,J.Med.Chem.2002,45,5005-5022.
6.Cosford N.D.P.,Tehrani L.,Roppe J.,Schweiger E.,Smith N.D.,Anderson J.,Bristow L.,Brodkin J.,Jiang X.H.,McDonald I.,Ran S.,Washburn M.,and Varney M.A.,J.Med.Chem.2003,46,204-206.
7.Shao B.,Victory S.,Ilyin V.I.,Goehring R.R.,Sun Q.,Hogenkamp D.,Hodges D.D.,Islam K.,Sha D.,Zhang C.,Nguyen P.,Robledo S.,Sakellaropoulos G.,and Carter R.B.,J..Med.Chem.2004,47,4277-4285.
8.Wei Z.L.,Xiao Y.,Yuan H.,Baydyuk M.,Petukhov P.A.,Musachio J.L.,Kellar K.J.,and Kozikowski A.P.,J.Med.Chem.2005,48,1721-1724.
9.Zhao H.,Serby M.D.,Xin Z.,Szczepankiewicz B.G.,Liu M.,Kosogof C.,Liu B.,Nelson L.T.J.,Johnson E.F.,Wang S.,Pederson T.,Gum R.J.,Clampit J.E.,Haasch D.L.,Abad-Zapatero C.,Fry E.H.,Rondinone C.,Trevillyan J.M.,Sham H.L.,and Liu G.,J.Med.Chem.2006,49,4455-4458.
10.Bemis,G.,Murcko,M.A.,J.Med.Chem.1996,39,2887.
11.Kohn,E.C.,Liotta,L.A.,US 637145(Chem Abstr:1991,115,248099)
12.Dong,H.S.,Wei,K.,Wang,Q.L.,Quan,B.J.Chin.Chem.Soc.2000,47,343-346.
13.Pedro Victory,Jos(?) I.Borrell,Anton Vidal-Ferran.Tetrahedron Lett.2001,31(22),3497-3505.
14.Mohammad M,Al-Arab.J.Heterocycllic.Chem.1989,26,1665.
1.Utimoto,K.;Obayashi,M.;Shishiyama,Y.;Inoue,M.;Nozaki,H.Tetrahedron Lett.1980,21,3389-3392.
2.Nagata,W.;Yoshioka,M.Org.React.1977,25,255,and the references cited therein.
3.Utimoto,K.;Wakabayashi,Y.;Horie,T.;Inoue,M.;Shishiyama,Y.;Obayashi,M.;Nozaki,H.Tetrahedron 1983,39,967-973.
4.Aurore Louder,Rakeshwar Bandichhor,Liangxing Wu,Kevin Burgess.Tetrahedron.2008 64,3642e3654.
5.Davis,Edward Mark;Ellis,James E.1998,WO 9815524.
6.Katsuhiko Hino,Yasutaka Nagai,Hitoshi Uno,Yoshinobu Masuda,Makoto Oka,Tadahiko Karasawa.J.Med.chem.1988,31,107-117.
7.Ciller,J.A.,Martin,N.,Quinteiro,M.,Seoane,C.,Soto,J.L.Organic preparations and procedures international.1986,18(4),227-36.
8.Salem,Mownir A.I.;Madlour,Hassan M.F.;Soliman,E1-Sayed A.;Mahmoud;Naglaa F.H.Heterocycles,2000,53(5),1129-1143.
9.Gao,Y.;Shi,D.Q.;Zhou,L.H.;Dai,G.Y.J.Org.Chem(Ch).1996,16,548.
10.Melot,J.M.;Boullet,F.M.;Foucaud,A.Tetrahedron Lett.1986,27,493.
11.Yamawaki,J.;Kawate,T.;Ando,T.;Hanafusa,T.Bull,Chem.Soc.Jpn.1983,56,1885.
12.Boullet,F.M,;Villemin,D.;Ricard,M.;Moison,A.;Foucaud,A.Tetrahedron 1985,41,1259.
13.(a) Yamawaki,J.;Yamawaki,J.;Kawate,T.;Sumi,S.;Hanafusa,T.Bull.Chem.Soc.Jpn 1982,55,2504;
(b) Yamawaki,J.;Ando,T.;Hanafusa,T.Chem.Lett.1981,(8),1143;
(c) Villemin,D.J.Chem.Soc.,Chem.Commun.1985,(13),870.
14.Roberto Ballinia,and Alessandro Palmieria.Adv.Synth.Catal.2006,348,1154 - 1156.
15.(a) Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Org.Chem(Ch).2002,22,909;
(b) Wang,X.S.;Shi,D.Q.;Tu,S.J.Synth.Commun.2003,33,119;
(c) Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Org.Chem(Ch) 2003,23,210;
(d) Wang,X.S.;Shi,D.Q.;Tu,S.J.Chin.J.Chem.2003,21,1114;
(e) Wang,X.S.;Shi,D.Q.;Yu,H.Z.;Wang,G.F.;Tu,S.J.Synth.Commun.2004,34,509.