2-(2-Arylvinyl)-7-substituted-quinazolin-4-(3H)-ones;Synthesis,reactions and antimicrobial activity

摘要

7-Chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one 3a on condensation with ethyl chloroformate, epichlorhydrin and isocyanates gives 7-chloro-3-[4-ethoxycarbonyloxyloxy)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 appropriate aldehyde yield 2-(2-arylvinyl)-7-chloro (or nitro)-3-[4-ethoxycarbonyloXy)phenyl]quinazolin-4(3H)ones 4b,c, 2-(2-arylvinyl)-7-chIoro-3-[4-(2,3-epoxypropoxy)phenyl]quinazolin-4(3H)-ones 5b,c and 7-chloro-2-[2-(4-chlorophenyl)vinyl]-3-[4-substituted aino-carbonyloxy)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)-phc-ny1]quinazo1in-4(3H)-ones 6c,e have also been obtained from 3b by refluxing with isocyanates. Further, 4,7-dichloroquinazolines 1O,b are obtained from 2-styrylquinazolinones 9a,b on treatment with POCl_3. Compounds lOa,b on condensation with glycine in the presence of pyridine yield 2-(2-arylvinyl)-7-chloro-4-carboxymethylaminoquinazolines lla,b which on fusion with Ac_2O/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.