Synthesis and rearrangement of triazinoquinazolines

✍ Scribed by Yehia A. Ibrahim; Ahmed H. M. Elwahy

• Book ID: 102228842
• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 327 KB
• Volume: 5
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520050203

✦ Synopsis

Selective syntheses of triazino [4,3-a]quinazolines 3ae and their isomeric triazino [3,2-b]quinazolines 4ae by cyclization of the appropriate a-keto acid hydrazones 2a-e under different reaction conditions are described. The angular triazinoquinazolines 3a-e were readily rearranged to the corresponding linear isomers 4a-e when heated in acetic anhydride in the presence of sodium acetate. This rearrangement was proposed to proceed via the intermediate isomeric triazino [3,4-b]quinaz:olines Sa-e. The N-methyl derivative 10 (of the intermediate Sb) was prepared and rearranged to 11, which is the N-methyl derivative of 4b.