腙参与的环加成反应研究进展
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摘要
环加成是两个或多个分子通过结合生成环状化合物的反应,它在有机合成中起着非常重要的作用。腙是一类重要的有机含氮化合物,作为有机合成中间体,它可与含有各种不饱和键的化合物发生不同类型的环加成反应来制备多种含氮杂环化合物;这些杂环化合物骨架广泛存在于医药、农药、材料和天然产物等分子结构中。主要对近几年腙与含有各种不饱和键化合物发生的各种环加成反应进行了综述,主要包括[3+3]、[3+2]、[3+4]、[4+2]和[4+3]等环加成反应,并对其发展方向进行了展望。
Cycloaddition is the formation of a cyclic compound via the reaction of two or more molecules,and it plays a very important role in organic synthesis.Hydrazones are very important nitrogen-contain compounds and they could react with various compounds having diverse unsaturated bonds to synthesize different nitrogen-contain heterocyclics.And these heterocyclic skeletons are widely presented in the molecular structure of medicine,pesticides,materials and natural products.The recent progress in the cycloadditions of hydrazones with diverse compounds mainly bearing various unsaturated bonds is summarized,including [3 + 3],[3+2],[3+4],[4+2]and [4+3]cycloaddition.Moreover,the prospects of future development are also discussed.
Cycloaddition is the formation of a cyclic compound via the reaction of two or more molecules,and it plays a very important role in organic synthesis.Hydrazones are very important nitrogen-contain compounds and they could react with various compounds having diverse unsaturated bonds to synthesize different nitrogen-contain heterocyclics.And these heterocyclic skeletons are widely presented in the molecular structure of medicine,pesticides,materials and natural products.The recent progress in the cycloadditions of hydrazones with diverse compounds mainly bearing various unsaturated bonds is summarized,including [3 + 3],[3+2],[3+4],[4+2]and [4+3]cycloaddition.Moreover,the prospects of future development are also discussed.
引文
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[17]XU P,WANG G Q,WU Z K,et al. Rh(Ⅲ)-catalyzed double C—H activation of aldehyde hydrazones:a route for functionalized 1H-indazole synthesis[J]. Chem. Sci.,2017,8(2):1 303-1 308.
[18]PRIETO A,BOUYSSI D,MONTEIRO N.Ruthenium-catalyzed tandem C—H fluoromethylation/cyclization of Nalkylhydrazones with CBr3F:access to 4-fluoropyrazoles[J].J.Org.Chem.,2017,82(6):3 311-3 316.
[19]LIU H L,JIA H,WANG B,et al.Synthesis of spirobidihydropyrazole through double 1,3-dipolar cycloaddition of nitrilimines with allenoates[J]. Org. Lett.,2017,19(18):4 714-4 717.
[20]ZHU S Y,ZHANG Y Z,WANG W,et al.Stereoselective synthesis of functionalized tetrahydro-1H-1,2-diazepines by N-heterocyclic carbene-catalyzed[3+4] annulation[J].Org.Lett.,2017,19(19):5 380-5 383.
[21]CHENG X,CAO X,XUAN J,et al. Silver(Ⅰ)-and base-mediated[3+3]-cycloaddition of C,N-cyclic azomethine imines with aza-oxyallyl cations[J]. Org.Lett.,2018,20(1):52-55.
[22]WANG Z Y,YANG Y Z,GAO F,et al.Synthesis of 5-(trifluoromethyl)pyrazolines by formal[4+1]-annulation of fluorinated sulfur ylides and azoalkenes[J].Org.Lett.,2018,20(4):9 34-9 37.
[23]GUO Z Y,JIA H,LIU H L,et al.A[4+3] annulation reaction of aza-o-quinone methides with arylcarbohydrazonoyl chlorides for synthesis of 2,3-dihydro-1H-benzo[e][1,2,4]triazepines[J]. Org. Lett.,2018,20(10):2 939-2 943.
[2]HACHEMIA E,MAMOUNI E,CATTOEN M,et al.Selective tsuji-trost type C-allylation of hydrazones:a straightforward entry into 4,5-dihydropyrazoles[J]. Chem. Commun.,2016,52(100):14 490-14 493.
[3]PENG X S,HUANG D F,WANG K H,et al.Synthesis of trifluoromethylated pyrazolidines by[3+2] cycloaddition[J].Org.Biomol.Chem.,2017,15(29):6 214-6 222.
[4]KONG Y F,TANG M,WANG Y,et al.Regioselective synthesis of 1,3,5-trisubstituted pyrazoles from N-alkylated tosylhydrazones and terminal alkynes[J].Org.Lett.,2014,16(2):576-579.
[5]PANDA S,MAITY P,MANNA D.Transition metal,azide,and oxidant-free homo-and hetero-coupling of ambiphilic tosylhydrazones to the regioselective triazoles and pyrazoles[J].Org.Lett.,2017,19(7):1 534-1 537.
[6]LI P,ZHAO J J,WU C R,et al.Synthesis of 3-substituted indazoles from arynes and N-tosylhydrazones[J]. Org.Lett.,2011,13(13):3 340-3 343.
[7]SENADI G C,HU W P,LU T Y,et al.I2-TBHP-catalyzed oxidative cross-coupling of N-sulfonyl hydrazones and isocyanides to 5-aminopyrazoles[J]. Org. Lett.,2015,17(6):1 521-1 524.
[8]CHEN Z K,LI H L,DONG W P,et al.I2-catalyzed oxidative coupling reactions of hydrazones and amines and the application in the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles[J].Org.Lett.,2016,18(6):1 334-1 337.
[9]HONG D,LIN X F,ZHU Y X,et al.Copper-catalyzed tandem nucleophilic ring-opening/intramolecular oxidativeamidation of N-tosylaziridines and hydrazones under aerobic conditions[J]. Org. Lett.,2009,11(24):5 678-5 681.
[10]GARVE L K B,PETZOLD M,JONES P G,et al.[3+3]-Cycloaddition of donor-acceptor cyclopropanes with nitrile imines generated in situ:access to tetrahydropyridazines[J].Org.Lett.,2016,18(3):564-567.
[11]CRESPIN L,BIANCALANA L,MORACK T,et al.Onepot acid-catalyzed ring-opening/cyclization/oxidation of aziridines with N-tosylhydrazones:access to 1,2,4-triazines[J].Org.Lett.,2017,19(5):1 084-1 087.
[12]MENG J,WEN M,ZHANG S W,et al.Unexpected O—H insertion of rhodium-azavinylcarbenes with N-acylhydrazones:divergent synthesis of 3,6-disubstituted-and3,5,6-trisubstituted-1,2,4-triazines[J]. J. Org. Chem.,2017,82(3):1 676-1 687.
[13]FERNNDEZ M,VICARIO J L,REYES E,et al. Organocatalytic enantioselective synthesis of 2,3-dihydropyridazines[J]. Chem. Commun.,2012,48(15):2 092-2 094.
[14]DING Z C,JU L C,YANG Y,et al.Silver(Ⅰ)-catalyzed tandem sigamatropic rearrangement/1,3-H shift/6πazaelectrocyclization of N-propargylic hydrazones:a mild synthetic route to 1,6-dihydropyridazines[J]. J. Org.Chem.,2016,81(9):3 936-3 941.
[15]ZHAO H W,PANG H L,ZHAO Y D,et al.Construction of 2,3,4,5-tetrahydro-1,2,4-triazines via[4+2] cycloaddition of a-halogeno hydrazones to imines[J].RSC.Adv.,2017,7(15):9 264-9 271.
[16]ZHAO H W,PANG H L,TIAN T,et al.Construction of2,3,4,7-tetrahydro-1,2,4,5-oxatriazepines via[4+3]cycloadditions of a-halogeno hydrazones with nitrones[J].Adv.Synth.Catal.,2016,358(11):1 826-1 832.
[17]XU P,WANG G Q,WU Z K,et al. Rh(Ⅲ)-catalyzed double C—H activation of aldehyde hydrazones:a route for functionalized 1H-indazole synthesis[J]. Chem. Sci.,2017,8(2):1 303-1 308.
[18]PRIETO A,BOUYSSI D,MONTEIRO N.Ruthenium-catalyzed tandem C—H fluoromethylation/cyclization of Nalkylhydrazones with CBr3F:access to 4-fluoropyrazoles[J].J.Org.Chem.,2017,82(6):3 311-3 316.
[19]LIU H L,JIA H,WANG B,et al.Synthesis of spirobidihydropyrazole through double 1,3-dipolar cycloaddition of nitrilimines with allenoates[J]. Org. Lett.,2017,19(18):4 714-4 717.
[20]ZHU S Y,ZHANG Y Z,WANG W,et al.Stereoselective synthesis of functionalized tetrahydro-1H-1,2-diazepines by N-heterocyclic carbene-catalyzed[3+4] annulation[J].Org.Lett.,2017,19(19):5 380-5 383.
[21]CHENG X,CAO X,XUAN J,et al. Silver(Ⅰ)-and base-mediated[3+3]-cycloaddition of C,N-cyclic azomethine imines with aza-oxyallyl cations[J]. Org.Lett.,2018,20(1):52-55.
[22]WANG Z Y,YANG Y Z,GAO F,et al.Synthesis of 5-(trifluoromethyl)pyrazolines by formal[4+1]-annulation of fluorinated sulfur ylides and azoalkenes[J].Org.Lett.,2018,20(4):9 34-9 37.
[23]GUO Z Y,JIA H,LIU H L,et al.A[4+3] annulation reaction of aza-o-quinone methides with arylcarbohydrazonoyl chlorides for synthesis of 2,3-dihydro-1H-benzo[e][1,2,4]triazepines[J]. Org. Lett.,2018,20(10):2 939-2 943.