Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/22152
Title: 2-(2-Arylvinyl)-7-substituted-quinazolin-4(3H)-ones: Synthesis, reactions and antimicrobial activity
Authors: El-Meligie, S.
El-Ansary, A K
Said, M M
Hussein, M M M
Issue Date: Jan-2001
Publisher: NISCAIR-CSIR, India
Abstract: 7-Chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one 3a on condensation with ethyl chloroformate, epichlorhydrin and isocyanates gives 7-chloro-3-[4-ethoxyearbonyloxy) phenyl]-2-methylquinazolin-4(3H)-one 4a, 7-chloro-3-[4-(2,3-epoxypropoxy)phenyl]-2-methylquinazolin -4(3H)-ones 5a and 7-chloro-3-[4-(substituted amino carbonyloxy) phenyl] -2-methylquinazolin-4-(3H-ones) 6a,b, respectively which on condensation with the appropri ate aldehyde yield 2-(2-arylvinyl)-7-chloro (or nitro)-3-[4-ethoxycarbonyloxy)phenyl]quina zolin-4(3H)-ones 4b,c, 2-(2-arylvinyl)-7-chloro-3-[4-(2,3-epoxypropoxy)phenyl]quinazolin-4 (3H)-ones 5b,c and 7-chloro-2-[2-(4-chlorophenyl)vinyl]-3-[4-substituted aminocarbonyloxy ) phenyl]quinazolin-4(3H)-ones 6c,d, respectively. Also the compounds 4b-d and 5b-d have been synthesized by reacting 2-(2-arylvinyl)-7-chloro (or nitro)-3-(4-hydroxyphenyl) quinazolin-4(3H)-ones 3b-d with ethyl chloroformate and epichlorohydrin, respectively. 7-Chloro-2-[2-(4-chlorophenyl)vinyl ]-3-[4-(substituted aminocarbonyloxy)-phenyl] quinazolin-4(3H)-ones 6c,e have also been obtained from 3b by refluxing with isocyanates. Further, 4,7-dichloroquinazolines 10,b are obtained from 2-styrylquinazolinones 9a,b on treatment with POCl3. Compounds 10a,b on condensation with glycine in the presence of pyridine yield 2-(2-arylvinyl)-7-chloro-4-carboxymethylaminoguinazolines 11a,b which on fusion with Ac2O/NaOAc afford 5-(2-arylvinyl)-8-chloro-imidazo[1,2-c]quinazolin-3-(2H)- ones 12a,b. Several compounds have been tested for their antimicrobial activity.
Page(s): 62-69
URI: http://hdl.handle.net/123456789/22152
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.40B(01) [January 2001]

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