Abstract
The diazonium salt of 3-(4-aminophenyl)-2-methyl-3H-quinazolin-4-one (2a) and its 6-bromo derivative 2b reacted with some active methylene compounds, namely ethyl acetoacetate (3), ethyl cyanoacetate (4) and acetylacetone (5), to afford the corresponding hydrazono quinazolinone derivatives 6-8. Treatment of 6a,b with hydrazine hydrate or phenyl hydrazine in refluxing ethanol afforded the corresponding pyrazolin-5-one derivatives of 3H-quinazolin-4-one 9a-d. Cyclization of 7a,b with hydrazine hydrate yielded the corresponding products 10a,b. Reaction of 8a,b with phenyl hydrazine or with urea afforded the corresponding derivatives 11a,b and 12a,b, respectively. Compounds 6-12 were identified by C,H,N analysis, IR, 1H-NMR, 13C-NMR and mass spectroscopy.
Highlights
3H-Quinazolin-4-ones and their derivatives have been reported to possess significant activity as antihypertensive [1], antifibrillatory, choleretic, antiphlogistic [2], antimitotic anticancer [3], antifungal [4,5] and anticonvulsant agents [6]
As a part of our continued program on the chemistry of 3H-quinazolin-4-one ring systems, we recently developed a simple and efficient approach to a wide range of such derivatives [15,16,17,18,19,20]
3-(4-Aminophenyl)-2-methyl-3H-quinazolin-4-one (1a) and its 6-bromo derivative 1b were prepared according to the literature procedures [21,22]
Summary
3H-Quinazolin-4-ones and their derivatives have been reported to possess significant activity as antihypertensive [1], antifibrillatory, choleretic, antiphlogistic [2], antimitotic anticancer [3], antifungal [4,5] and anticonvulsant agents [6]. They have been successfully tested as CNS depressants [7], muscle relaxants [8] and for their antineoplastic activity [9]. These results prompted us to synthesize a series of novel 3H-quinazolin-4-one derivatives containing a pyrazolinone, pyrazole or pyrimidinone ring, with the aim of obtaining some novel heterocyclic systems with potentially enhanced biological properties
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