Pyrimido[5,4-b]quinolines. III. Synthesis of 10-alkyl-substituted 10-deazaalloxazines

✍ Scribed by C. K. Chu; T. J. Bardos

• Book ID: 112125106
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1977
• Tongue: English
• Weight: 404 KB
• Volume: 14
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570140621

✦ Synopsis

Abstract

A general method for the synthesis of 10‐alkyl‐substituted 10‐deazaalloxazines (VIII) and the related chemistry are described. 4‐Alkyl‐substituted 3‐aminoquinolines (IV) were reacted with benzoyl chloride and potassium cyanide in methylene chloride‐water mixture to obtain Reissert compounds (V) which were hydrolyzed with a mixture of hydrobromic acid and acetic acid, and subsequently with 20% potassium hydroxide to give the corresponding 3‐aminoquinaldic acids (VII). Cyclization with urea gave the 10‐deazaalloxazines (VIII). Oxidation, hydroxylation and alkylation reactions of the 10‐methyl derivatives (VIIIa,b) and of their quinaldic acid precursors are also reported.