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Molecules 2003, 8(4), 363-373; doi:10.3390/80400363
Article

Synthesis of Novel 3H-Quinazolin-4-ones Containing Pyrazolinone, Pyrazole and Pyrimidinone Moieties

* , ,  and
Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt
* Author to whom correspondence should be addressed.
Received: 22 September 2002 / Revised: 7 December 2002 / Accepted: 8 April 2003 / Published: 30 April 2003
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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.
Keywords: 3-(4-Aminophenyl)-2-methyl-3H-quinazolin-4-one; bromo derivative; active methylene compounds; cyclization; nitrogen nucleophiles 3-(4-Aminophenyl)-2-methyl-3H-quinazolin-4-one; bromo derivative; active methylene compounds; cyclization; nitrogen nucleophiles
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Saleh, M.A.; Abdel-Megeed, M.F.; Abdo, M.A.; Shokr, A.-B.M. Synthesis of Novel 3H-Quinazolin-4-ones Containing Pyrazolinone, Pyrazole and Pyrimidinone Moieties. Molecules 2003, 8, 363-373.

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