Tandem reactions of N'-(2-alkynylbenzylidene)hydrazides with silyl enolates: a facile route to H-pyrazolo[5,1-a]isoquinolines

Xingxin Yu; Zhiyuan Chen; Xiaodi Yang; Jie Wu

doi:10.1021/cc1000314

Tandem reactions of N'-(2-alkynylbenzylidene)hydrazides with silyl enolates: a facile route to H-pyrazolo[5,1-a]isoquinolines

J Comb Chem. 2010 May 10;12(3):374-8. doi: 10.1021/cc1000314.

Authors

Xingxin Yu¹, Zhiyuan Chen, Xiaodi Yang, Jie Wu

Affiliation

¹ Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.

PMID: 20337469
DOI: 10.1021/cc1000314

Abstract

A silver triflate-catalyzed tandem reaction of N'-(2-alkynylbenzylidene)hydrazide with silyl enolate is described, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good to excellent yields. Intramolecular cyclization, nucleophilic addition, condensation, and aromatization may be involved in the reaction process.

Publication types

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

MeSH terms

Alkynes / chemistry*
Benzylidene Compounds / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Hydrazines / chemistry*
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry
Mesylates / chemistry
Models, Chemical
Pyrazoles / chemical synthesis*
Pyrazoles / chemistry
Silicon Compounds / chemistry*

Substances

Alkynes
Benzylidene Compounds
Hydrazines
Isoquinolines
Mesylates
Pyrazoles
Silicon Compounds
trifluoromethanesulfonic acid