Synthesis of some novel pyrimidine, thiophene, coumarin, pyridine and pyrrole derivatives and their biological evaluation as analgesic, antipyretic and anti-inflammatory agents

摘要

Pyrimidine derivative 3 was afforded through the reaction of compound ( 1 ) with 5-ureidohydantion ( 2 ). Product 3 underwent a cyclization to produce fused pyrimidine derivative 7 , although the latter product 7 was synthesized through one step via the reaction of compound ( 1 ) with 5-ureidohydantion ( 2 ) using another catalyst. Compound 3 was oriented to react with cyclic ketones 8a , b in the presence of elemental sulfur, salicylaldehyde ( 10 ), aryldiazonium chlorides 12a , b and ω-bromo-4-methoxy- acetophenone ( 14 ), which afforded, fused thiophene derivatives 9a , b , coumarin derivative 11 , arylhdrazono derivatives 13a , b and 4-methoxyphenyl butenyl derivative 15, respectively. The latter product 15 was reacted with either potassium cyanide ( 16a ) or potassium thiocyanide ( 16b ) to form cyano and thiocyano derivatives 17a , b , respectively. Compound 17a underwent further cyclization to afford pyridopyrimidine derivative 19. Compound 15 was reacted with either hydrazine ( 20a ) or phenylhydrazine ( 20b ) to produce hydrazo derivatives 21a , b and these products were cyclize to produce pyrrole derivatives 23a , b . Finally, 5-ureidohydantion ( 2 ) was reacted with compounds 24a , b , c to afford pyrimidine derivatives 25a , b , c . The structures of the synthesized compounds were confirmed using IR, 1 H NMR, 13 C NMR and mass spectrometry techniques. Compounds 11 and 19 have promising as analgesic and antipyretic activities.