Synthesis of Functionalized 2-Aminopyrroles by Lewis Acid Catalyzed Ring-opening of 1,1,2,3-Tetrasubstituted Cyclopropanes with Arylamines

被引：14

作者：

Han Ying ^{[1
]}

Fu Qin ^{[1
]}

Tang Wanquan ^{[1
]}

Yan Chaoguo ^{[1
]}

机构：

[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2012年 / 30卷 / 08期

基金：

中国国家自然科学基金;

关键词：

cyclopropane; pyrrole; ring-opening reaction; catalysis; domino reaction; DIASTEREOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITIONS; ALDEHYDES; TETRAHYDROFURANS; CONSTRUCTION; EFFICIENT; IMINES;

D O I：

10.1002/cjoc.201200229

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Under the catalysis of Lewis acid Co(ClO4)2 the reaction of the sterically hindered 1,1,2,3-tetrasubstituted cyclopropanes with arylamines in refluxing THF gave the functionalized 2-aminopyrroles with sequential ring-opening of cyclopropane, nucleophilic substitution, nucleophilic addition of cyano group and recyclization processes.

引用

页码：1867 / 1872

页数：6

共 27 条

[1] 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

[2] 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

[3] 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

[4] 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

[5] 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

[6] 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

[7] A novel ring-opening based tandem domino process of an activated vinyl cyclopropane [J].

Du, Ding ;

Wang, Zhongwen .

TETRAHEDRON LETTERS, 2008, 49 (06) :956-959

[8] Efficient synthesis of polysubstituted pyrrole-3-carbonitriles via reactions of 1,1-dicyano-2,3-diarylcyclopropanes with aromatic imines [J].

Fu, Qin ;

Yan, Chao-Guo .

TETRAHEDRON LETTERS, 2011, 52 (34) :4497-4500

[9] Synthesis of Functionalized Dihydrothiophenes from Doubly Activated Cyclopropanes Using Tetrathiomolybdate as the Sulfur Transfer Reagent [J].

Gopinath, Purushothaman ;

Chandrasekaran, Srinivasan .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (02) :700-703

[10] A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones [J].

Gupta, Archana ;

Yadav, Veejendra K. .

TETRAHEDRON LETTERS, 2006, 47 (46) :8043-8047

← 1 2 3 →