Tetrahedron

Reaction of chromone-3-carbaldehyde with α-amino acids—syntheses of 3-and 4-(2-hydroxybenzoyl) pyrroles

AGPR Figueiredo, AC Tomé, AMS Silva, JAS Cavaleiro

Index: Figueiredo, Andrea G.P.R.; Tome, Augusto C.; Silva, Artur M.S.; Cavaleiro, Jose A.S. Tetrahedron, 2007 , vol. 63, # 4 p. 910 - 917

Full Text: HTML

Citation Number: 25

Abstract

Azomethine ylides generated from the reaction of chromone-3-carbaldehyde with α-amino acids undergo 1, 5-electrocyclization reactions to afford 3-and 4-(2-hydroxybenzoyl) pyrroles. These ylides can be trapped with dipolarophiles in 1, 3-dipolar cycloaddition reactions to yield chromonyl pyrrolidines. The reaction of chromone-3-carbaldehyde with methyl glycinate gives a mixture of pyrrole, pyridine, and 3-aza-9-xanthenone derivatives.