Synthesis of [1]benzopyrano[4,3-b]pyrrol-4(1H)-ones from N(alpha)-(2-oxo-2H-1-benzopyran-4-yl)Weinreb alpha-aminoamides

Authors
Alberola, A Alvaro, R Ortega, AG Sadaba, ML Sanudo, MC
Citation
A. Alberola et al., Synthesis of [1]benzopyrano[4,3-b]pyrrol-4(1H)-ones from N(alpha)-(2-oxo-2H-1-benzopyran-4-yl)Weinreb alpha-aminoamides, TETRAHEDRON, 55(46), 1999, pp. 13211-13224
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
46
Year of publication
1999
Pages
13211 - 13224
Database
ISI
SICI code
0040-4020(19991112)55:46<13211:SO[FN>2.0.ZU;2-A
Abstract
N(alpha)-(2-Oxo-2H-1-benzopyran-4-yl)Weinreb-alpha-aminoamides were prepare d from 4-chlorocoumarin and alpha-aminoacid derivatives. Their reaction wit h organometallic compounds (RLi or RMgBr) and subsequent cyclization of ket ones thus obtained, give [1]benzopyrano[4,3-b]pyrrol-4(1H)-ones. Starting f rom proline derivatives, simultaneously with the pyranone-pyrrole fusion, w e establish an interesting procedure for the formation of pyrrolizines. (C) 1999 Elsevier Science Ltd. All rights reserved.