Synthesis of New Rhodanine, Thiazole, Quinazolin-4-One, Imidazolone and Pyranothiazole Derivatives Incorporating Antipyrine Moiety as Antimicrobial Agents

Abstract

A new series of heterocycles incorporating antipyrine moiety were synthesized via reactions of 4-aminoantipyrine 1 with carbon disulphide then alkylation and /or chloroacetic acid to produce dithiocarbamate and rhodanine 3, 4 and 9. Multi-component reaction (MCR) of 4-aminoantipyrine with carbon disulfide and DMAD afforded rhodanine 7. The interaction of 9 with diazonium salt, DMF-DMA, nitrous acid and aromatic aldehydes to give thiazolidinone derivatives 10, 11, 13 and 14, respectively. Pyranothiazole 16 was prepared from reaction of 9 with cinamonitrile 15. Thiazolidinone 18 and thiazole 19 derivatives were obtained from reactions of 9 with phenyl isothiocyanate in the presence of KOH then halogenated the pot salt with ethyl bromoacetate and chloroacetone, respectively. Thiourea derivative 20 was prepared from reaction of methyl dithiocarbamate 3 with 4-aminoantipyrine. pyrimidine derivatives 21 and 22 were obtained from cyclocondensation of 3 with dimer of ethyl cyanoacetate and malononitrile. Pyrazolotriazine 24 was prepared from interaction of 3 with hydrazine hydrate. copounds 26 and 28 were obtained via reaction of 3 with glycine and anthranilic acid. Compounds 30, 32 and 34 were prepared via reaction of thiourea 20 with EAA, ECA and DMAD. Reaction of diazonium chloride of 1 with NaN3 afforded azide 36 which rearranged to triazine 39. The structures of the newly synthesized compounds were elucidated via elemental analysis and spectral data. The synthesized products were evaluated for their antimicrobial and anti-fungal activity.