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A study concerning the synthesis, basicity and hydrolysis of 4‐amino‐2‐( N , N ‐diethylamino)quinazoline derivatives
Author(s) -
Zieliński Wojciech,
Kudelko Agnieszka
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390627
Subject(s) - chemistry , cyanamide , hydrolysis , quinazoline , medicinal chemistry , aqueous solution , catalysis , organic chemistry
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.