1,3-Dipolar Cycloaddition Reactions in Heterocyclic Synthesis. Synthesis of [1-[4-(thiazolyl/imidazothiazolyl/triazolyl)phenyl]-1H-pyrazole-3,4-dicarboxylate esters from 3-(4-acetylphenyl)sydnone

Abstract

Cycloaddition of 3-(4-acetylphenyl)sydnone (1) with DMAD gave dimethyl 1-(4-acetylphenyl)-1H-pyrazole-3,4-dicarboxylate (2), which on bromination yielded the corresponding monobromoacetyl (3) and dibromoacetyl (4) derivatives. Both compounds 3 and 4 on reaction with thiourea and thioacetamide afforded the 2-amino- (5) and the 2-methyl- (6) thiazole derivatives respectively, while compound 3 on reaction with 2-aminothiazole gave the imidazothiazole 7. Compound 3 was converted into its azide (8), which on 1,3-dipolar cycloaddition with DMAD afforded the 1,2,3-triazole-4,5-dicarboxylate (9).