Nitroimidazoles: Part V. 1(-1-Methyl-5-nitroimldazol-2-yl)-1,2,4-triazolidin-3,5-diones and analogues

Abstract

Condensation of 1-methyl-2-methylsulphonyl-5-nitroimidazole (1) with the sodium salts of triazolidinediones affords the derivatives 2a-i; similar reaction with the sodium salts of thiazolidinone, 2-iminothiazolidine, pyrrolidinone, oxazolidinone and it's 2-methyl and 2-chloromethyl analogues leads to the formation of products 3-8 respectively. Under the reaction conditions 3 is opened by dimethylamide ion to form 10, and 6 by methyl sulfinate ion to provide 13 respectively. Additionally, 6 is hydrolysed to the amine (12). Cyclic sulphamides (17-22) undergo reaction with 1 to provide nitroimidazoles (23-28).