Reaction of polyhaloalkyl-substituted chromones, pyrones, and furanones with salicylaldehydes as a direct route to fused 2H-chromenes

Vyacheslav Ya Sosnovskikh; Vladislav Yu Korotaev; Dmitry L Chizhov; Igor B Kutyashev; Danil S Yachevskii; Olga N Kazheva; Oleg A Dyachenko; Valery N Charushin

doi:10.1021/jo060459x

Reaction of polyhaloalkyl-substituted chromones, pyrones, and furanones with salicylaldehydes as a direct route to fused 2H-chromenes

J Org Chem. 2006 Jun 9;71(12):4538-43. doi: 10.1021/jo060459x.

Authors

Vyacheslav Ya Sosnovskikh¹, Vladislav Yu Korotaev, Dmitry L Chizhov, Igor B Kutyashev, Danil S Yachevskii, Olga N Kazheva, Oleg A Dyachenko, Valery N Charushin

Affiliation

¹ Department of Chemistry, Ural State University, 620083 Ekaterinburg, Russian Federation. vyacheslav.sosnovskikh@usu.ru

PMID: 16749786
DOI: 10.1021/jo060459x

Abstract

Polyhaloalkyl-substituted chromones, gamma-pyrones, and beta-furanones react with salicylaldehydes in the presence of piperidine to give a wide variety of fused 2H-chromenes in good yields. This novel annulation reaction presumably proceeds by a tandem intermolecular oxa-Michael addition and subsequent intramolecular Mannich condensation.

Publication types

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

MeSH terms

Aldehydes / chemistry
Benzopyrans / chemical synthesis*
Chromones / chemistry
Furans / chemistry
Pyrones / chemistry

Substances

Aldehydes
Benzopyrans
Chromones
Furans
Pyrones
salicylaldehyde