synthesis of novel 3h-quinazolin-4-ones containing pyrazolinone, pyrazole and pyrimidinone moieties合成新型3包含pyrazolinone h-quinazolin-4-ones,吡唑和pyrimidinone根.pdfVIP

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synthesis of novel 3h-quinazolin-4-ones containing pyrazolinone, pyrazole and pyrimidinone moieties合成新型3包含pyrazolinone h-quinazolin-4-ones,吡唑和pyrimidinone根.pdf

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synthesis of novel 3h-quinazolin-4-ones containing pyrazolinone, pyrazole and pyrimidinone moieties合成新型3包含pyrazolinone h-quinazolin-4-ones,吡唑和pyrimidinone根

Molecules 2003, 8, 363-373 molecules ISSN 1420-3049 / Synthesis of Novel 3H-Quinazolin-4-ones Containing Pyrazolinone, Pyrazole and Pyrimidinone Moieties Mohamed A. Saleh*, Mohamed F. Abdel-Megeed, Mohamed A. Abdo and Abdel-Basset M. Shokr Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt. Tel.: +203556576, Fax: +2040-3350804 *Author to whom corresponding should be addressed; E-mail: MAHSALEH@ Received: 22 September 2002; in revised form 7 December 2002 / Accepted: 8 April 2003/ Published: 30 April 2003 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, 1 respectively. Compounds 6-12 were identified by C,H,N analysis, IR, H-NMR, 13C-NMR and mass spectroscopy.