A study concerning the synthesis, basicity and hydrolysis of 4-amino-2-(N,N-diethylamino)quinazoline derivatives

✍ Scribed by Wojciech Zieliński; Agnieszka Kudelko

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 40 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390627

✦ Synopsis

Abstract

A group of 2‐(N,N‐diethylamino)‐4‐aminoquinazoline derivatives have been synthesized in the reaction of N^1^,N^1^‐diethyl‐N^2^‐arylchlorocarboxyamidines with cyanamide in the presence of T1Cl~4~ as a catalyst. Such quinazolines decompose into the corresponding quinazolones in dilute aqueous HC1 solutions at higher temperature. Hydrolysis rates of 2‐(N,N‐diethylamino)‐4‐aminoquinazoline and 2‐(N,N‐diethylamino)‐4‐(N,N‐dimethylamino)‐quinazoline have been determined to observe the influence of substituents at the 4‐amino group upon the hydrolysis. pK~a~ values have been also determined for these compounds and analyzed in conjunction with the Hammett σ constants.