SYNTHESIS AND REACTIONS OF N-CHLOROMETHYL-1,2,4-TRIAZOLES WITH SULFUR AND OXYGEN NUCLEOPHILES

Abstract

2-Chloromethyl-1,2,4-triazole-3-thione derivatives (1 and 2) were synthesized through the hydroxy-methyl derivatives, and reacted with alkyl, aryl and heteroaryl thiols to give the corresponding sulfides (3–15). Compounds 1 and 2 were reacted with sodium alkoxides and phenoxide affording the corresponding ethers (19–24). Transformation of C˭S to C˭O has been achieved by the action of mercuric acetate. Condensation of compounds 1 and 2 with hydrazine, phenylhydrazine and hydroxylamine yielded bicyclic condensation products 27–32. Activity of the newly synthesized compounds against different kinds of fungi has been investigated in vitro.

Key Words:

• 2-Chloromethyl-1,2,4-triazole-3-thione
• thiols
• alkoxides