Synthesis of Spiroheterocycles Containing Thiadiazole Thiadiazine and Triazine Moieties from Nitrilimines

Abstract

A series of 5-substituted 1-methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6-ones was prepared by the reaction of α-amino acid methyl esters with appropriate nitrilimines and treated with phosphorus pentasulfide to afford 5-substituted 1-methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6-thiones. When 1,2,4-triazin-6-thiones were allowed to react with nitrilimine, the novel 4,6-dimethyl-2,8-di-phenyl-10-substituted-1-thia-3,4,6,7,9-pentaazaspiro[4.5]dec-2,7-dienes were obtained and confirmed by their elemental analyses and spectral data. Some of the synthesized compounds were tested in vitro for their antimicrobial activity.

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GRAPHICAL ABSTRACT