PREPARATION OF CYCLIC OPROPYL-4-OXOQUINAZOLIN-3-YL)AMINO-BETA-KETOESTERS - FURTHER OXIDATION WITH LEAD-TETRAACETATE IN DICHLOROMETHANE AND IN METHANOL LEADING TO RING-EXPANSION AND RING-CLEAVAGE PRODUCTS, RESPECTIVELY

Authors
ATKINSON RS BARKER E EDWARDS PJ THOMSON GA
Citation
Rs. Atkinson et al., PREPARATION OF CYCLIC OPROPYL-4-OXOQUINAZOLIN-3-YL)AMINO-BETA-KETOESTERS - FURTHER OXIDATION WITH LEAD-TETRAACETATE IN DICHLOROMETHANE AND IN METHANOL LEADING TO RING-EXPANSION AND RING-CLEAVAGE PRODUCTS, RESPECTIVELY, Tetrahedron letters, 35(42), 1994, pp. 7863-7866
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
42
Year of publication
1994
Pages
7863 - 7866
Database
ISI
SICI code
0040-4039(1994)35:42<7863:POCO>2.0.ZU;2-L
Abstract
Cyclic beta-ketoesters e.g. 7 and the enol silyl ether 18 are converte d to the corresponding alpha-(quinazolinonyl)amino (alpha-Q'NH) deriva tives 10 and 19 respectively by reaction with the 3-acetoxyaminoquinaz olinone 6: further oxidation of 10 and 19 with lead tetra-acetate in d ichloromethane gave ring-expanded products 15 and 20 respectively but with methanol as solvent the corresponding ring-cleaved products 21 an d 22 are obtained: radical intermediates do not appear to be involved.