3-Phenacylideneoxindoles with tosylmethyl isocyanide and MeOH through C-C bond cleavage: facile synthesis of pyrrole and 2H-pyrrolo[3,4-c]quinoline derivatives

被引：27

作者：

Wang, Rong ^{[1
]}

Xu, Xiao-Ping ^{[1
]}

Meng, Hua ^{[1
]}

Wang, Shun-Yi ^{[1
]}

Ji, Shun-Jun ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-C Bonds cleavage; 3-Phenacylideneoxindoles; Tosylmethyl isocyanide; Pyrrole; 2H-Pyrrolo[3,4-c]quinolines; ONE-POT SYNTHESIS; ONE-STEP SYNTHESIS; CASPASE-3; INHIBITORS; GASTRIC (H+/K+)-ATPASE; REVERSIBLE INHIBITORS; PYRROLOQUINOLINE CORE; COUPLING REACTIONS; TRICYCLIC CORE; MARTINELLINE; CHEMISTRY;

D O I：

10.1016/j.tet.2012.11.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel reaction of 3-phenacylideneoxindoles (1) with tosylmethyl isocyanide (2a) and MeOH through C-C bond cleavage has been developed. The reaction proceeded under mild conditions, providing a powerful synthetic tool for the construction of pyrrole derivatives (3) from easily accessible starting materials and synthesis of 2H-pyrrolo[3,4-c]quinolines (4) by further dehydration of 3. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1761 / 1766

页数：6

共 47 条

[1]

Alisi M. A., 2010, [No title captured], Patent No. [WO2010012611A1, 2010012611]

[2]

BARTON DHR, 1990, TETRAHEDRON, V46, P7587

[3] Multi-component coupling reactions:: synthesis of a guanidine containing analog of the hexahydropyrrolo[3,2-c] quinoline alkaloid martinelline [J].