Access to quinazolines from 2-nitrobenzaldehyde and arylamines

Citation
Ja. Valderrama et al., Access to quinazolines from 2-nitrobenzaldehyde and arylamines, HETEROCYCLE, 51(9), 1999, pp. 2193-2201
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
9
Year of publication
1999
Pages
2193 - 2201
Database
ISI
SICI code
0385-5414(19990901)51:9<2193:ATQF2A>2.0.ZU;2-4
Abstract
A synthesis of N-(2-nitrobenzyl) acetanilide (5) and (11) from 2-nitrobenza ldehyde and aromatic amines is reported. The reaction of amides (5) and (11 ) with iron in acetic acid-ethanol-water provided the corresponding 3-pheny l-pi 1,2,3,4-tetrahydroquinazolines (7) and (12). Reductive cyclization of 1-acetyl-2-(2-nitrophenyl) -benzimidazol (16) to benzimidazo[1,2-c]quinazol ine (19) and benzimidazol (20) is described.