A FACILE SYNTHESIS OF PYRAZOLE, ISOXAZOLE AND PYRIMIDINE ORTHO-DICARBOXYLIC ACID-DERIVATIVES VIA BETA-ENAMINOKETOESTERS

Authors
VERONESE AC CALLEGARI R MORELLI CF VICENTINI CB
Citation
Ac. Veronese et al., A FACILE SYNTHESIS OF PYRAZOLE, ISOXAZOLE AND PYRIMIDINE ORTHO-DICARBOXYLIC ACID-DERIVATIVES VIA BETA-ENAMINOKETOESTERS, Tetrahedron, 53(42), 1997, pp. 14497-14506
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
42
Year of publication
1997
Pages
14497 - 14506
Database
ISI
SICI code
0040-4020(1997)53:42<14497:AFSOPI>2.0.ZU;2-L
Abstract
beta-Alkoxycarbonyl-beta-enaminoketoesters 1a,b react with hydrazines to give pyrazole ortho-dicarboxylic acid derivatives 3, 4 and 5. Simil arly la reacts with hydroxylamine to give isoxazole 6 and with amidine s and guanidine to give pyrimidine ortho-dicarboxylic acid monoesters 7a-c. The total or partial hydrolysis oi selected heterocycles afforde d the dicarboxylic acids 8, 9 and 10 and the dicarboxylic acid monoest ers 11 and 12. (C) 1997 Elsevier Science Ltd.