Assembly of substituted 3-methyleneisoindolin-1-ones via a CuI/l-proline-catalyzed domino reaction process of 2-bromobenzamides and terminal alkynes

Li Li; Miao Wang; Xiaojing Zhang; Yongwen Jiang; Dawei Ma

doi:10.1021/ol9000922

Assembly of substituted 3-methyleneisoindolin-1-ones via a CuI/l-proline-catalyzed domino reaction process of 2-bromobenzamides and terminal alkynes

Org Lett. 2009 Mar 19;11(6):1309-12. doi: 10.1021/ol9000922.

Authors

Li Li¹, Miao Wang, Xiaojing Zhang, Yongwen Jiang, Dawei Ma

Affiliation

¹ Shenyang Pharmaceutical University, 103 Wenhua Lu, Shenyang 110016, China.

PMID: 19226134
DOI: 10.1021/ol9000922

Abstract

CuI/l-proline catalyzed coupling of 2-bromobenzamides and terminal alkynes in i-PrOH (or DMF and DMSO) at 85-110 degrees C and subsequent additive cyclization produces substituted 3-methyleneisoindolin-1-ones. Variation of N-substituents, aromatic ring, and methylene part is possible by using suitable starting materials.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Benzamides / chemistry*
Combinatorial Chemistry Techniques
Copper / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Proline / chemistry*

Substances

Alkynes
Benzamides
Indoles
Copper
Proline