SYNTHESIS AND PROPERTIES OF THIAZOLE HALOHYDRAZONES. 2. INTERACTION OF 2-α-CHLOROBENZYLIDENEHYDRAZINO-4-ETHOXY-CARBONYLTHIAZOLE WITH NUCLEOPHILES

Article abstract of DOI:10.1007/BF01165020

In the interaction of 2-α-chlorobenzylidenehydrazino-4-ethoxycarbonylthiazole with nucleophiles, two competing reactions take place: 1) nucleophilic replacement of the chlorine atom to form the corresponding substitution product; 2) elimination of a hydrogen chloride molecule, concluding in cyclization of the intermediate nitrilimine to form 3-phenyl-5-ethoxycarbonylthiazolo<2,3-c>-1,2,4-triazole.The direction taken by the interaction depends on the nature of the nucleophile and is determined primarily by the ratio of basicity and nucleophilicity of the agent.