Convenient synthesis of 1a,1b,2,5-tetrahydro-1H-5a-aza-cyclopropa[a]indenes by base promoted cyclodimerization of 1,1-dicyano-2-aryl-3-benzoylcyclopropanes

被引:9
作者
Han, Ying [1 ]
Tang, Wan-Quan [1 ]
Guo, Ling-Yu [1 ]
Yan, Chao-Guo [1 ]
机构
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
基金
中国国家自然科学基金;
关键词
Cyclopropane; Pyridine ylide; Ring-opening reaction; Cyclodimerization; Domino reaction; MGI2-MEDIATED RING EXPANSIONS; DONOR-ACCEPTOR CYCLOPROPANES; ACTIVATED CYCLOPROPANES; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; EFFICIENT; CONSTRUCTION; DIMERIZATION; METHODOLOGY;
D O I
10.1016/j.tet.2014.06.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,1-Dicyano-2-aryl-3-benzoylcyclopropanes in acetonitrile in the presence of triethylamine underwent cyclodimerization reaction to afford the novel polyfunctionalized 1a,1b,2,5-tetrahydro-1H-5a-aza-cyclopropa[a]indenes in moderate yields. These polycyclic compounds can be more conveniently synthesized by the one-pot domino reaction of N-phenacylpyridinium bromides with arylidene malononitriles. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6663 / 6668
页数:6
相关论文
共 52 条
[1]  
Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
[2]  
2-5
[3]   A combinatorial scaffold approach based upon a multicomponent reaction [J].
Bertozzi, F ;
Gundersen, BV ;
Gustafsson, M ;
Olsson, R .
ORGANIC LETTERS, 2003, 5 (09) :1551-1554
[4]   A novel metal iodide promoted three-component synthesis of substituted pyrrolidines [J].
Bertozzi, F ;
Gustafsson, M ;
Olsson, R .
ORGANIC LETTERS, 2002, 4 (18) :3147-3150
[5]   Complexity-Building Annulations of Strained Cycloalkanes and C=O π Bonds [J].
Campbell, Matthew J. ;
Johnson, Jeffrey S. ;
Parsons, Andrew T. ;
Pohlhaus, Patrick D. ;
Sanders, Shanina D. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19) :6317-6325
[6]   A facile preparation of trans-1,2-cyclopropanes containing p-trifluoromethylphenyl group and its application to the construction of pyrazole and cyclopropane ring fused pyridazinone derivatives [J].
Cao, Weiguo ;
Zhang, Hui ;
Chen, Jie ;
Deng, Hongmei ;
Shao, Min ;
Lei, Lu ;
Qian, Jiaxian ;
Zhu, Yuan .
TETRAHEDRON, 2008, 64 (28) :6670-6674
[7]   Diastereoselective synthesis of pyrrolidines via the Yb(OTf)3 catalyzed three-component reaction of aldehydes, amines, and 1,1-cyclopropanediesters [J].
Carson, CA ;
Kerr, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (20) :8242-8244
[8]   [3+2] Cyclodimerization of 2-arylcyclopropane-1,1-diesters. Lewis acid induced reversion of cyclopropane umpolung [J].
Chagarovskiy, Alexey O. ;
Ivanova, Olga A. ;
Budynina, Ekaterina M. ;
Trushkov, Igor V. ;
Melnikov, Mikhail Ya .
TETRAHEDRON LETTERS, 2011, 52 (34) :4421-4425
[9]   Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to 2-Styrylmalonates [J].
Chagarovskiy, Alexey O. ;
Ivanova, Olga A. ;
Rakhmankulov, Eduard R. ;
Budynina, Ekaterina M. ;
Trushkov, Igor V. ;
Melnikov, Mikhail Ya. .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3179-3184
[10]   Lewis acid-catalyzed reactions of donor-acceptor cyclopropanes with furan derivatives [J].
Chagarovskiy, Alexey O. ;
Budynina, Ekaterina M. ;
Ivanova, Olga A. ;
Grishin, Yuri K. ;
Trushkov, Igor V. ;
Verteletskii, Pavel V. .
TETRAHEDRON, 2009, 65 (27) :5385-5392