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

Molecules

Mohamed A. Saleh¹  Mohamed F. Abdel-Megeed²  Mohamed A. Abdo² 

[1] id="af1-molecules-08-00363">Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt. Tel.: [phone], Fax: [phone]

关键词: 3-(4-Aminophenyl)-2-methyl-3H-quinazolin-4-one;    bromo derivative;    active methylene compounds;    cyclization;    nitrogen nucleophiles;   

DOI  :  10.3390/80400363

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
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