A SIMPLE APPROACH TO PYRIMIDINE AND QUINAZOLINE DERIVATIVES BY [4-DIAZADIENES AND ENAMINES(2] CYCLOADDITION OF 1,3)

Authors
BARLUENGA J TOMAS M BALLESTEROS A LOPEZ LA
Citation
J. Barluenga et al., A SIMPLE APPROACH TO PYRIMIDINE AND QUINAZOLINE DERIVATIVES BY [4-DIAZADIENES AND ENAMINES(2] CYCLOADDITION OF 1,3), Heterocycles, 37(2), 1994, pp. 1109-1120
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
37
Issue
2
Year of publication
1994
Pages
1109 - 1120
Database
ISI
SICI code
0385-5414(1994)37:2<1109:ASATPA>2.0.ZU;2-2
Abstract
The reaction of 2-trimethylsilyloxy- (1) and 2-trimethylsilylthio-1,3- diazabutadienes (2) with enamines derived from aliphatic aldehydes lea ds regio-and stereoselectively to substituted tetrahydropyrimidin-2(1H )-ones (3) and thiones (4) in high yields. Extension of this cycloaddi tion to cyclic enamines, e.g. derived from cyclohexanone, leading to q uinazoline derivatives (9-10) is also described. These heterocycles un dergo hydrolysis and dehydration to 3,4-dihydropyrimidine (7-8) and 3, 4,5,6,7,8-hexahydroquinazoline (11-12) derivatives.