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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 (CC BY 3.0).
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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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