Synthesis and antimicrobial activity of novel spirotetrazines with thiazole and 4-thiazolidinone moiety

Hemant Kumar and Ram Pal Chaud

Abstract

The facile synthesis of 3-methyl-(III), 3,7-dimethy-6'(7'H)-oxo spiro[cyclohexane-1,3'(4'H)-[2H] thiazolo[3,2-b]-s-tetrazines](IV) and 3-methyl-6,7'-dihydro spiro[cyclohexan-1,3'(4'H)- [2H]thiazolo [3,2-b]-s-tetrazine](V)have been accomplished by reaction of 3-methyl-7,8,10,11- tetaaza spiro[5,5]undecane-9-thione (II) with chloroacetic acid, α-bromopropionic acid, 1,2- dibromoethane respectively. A reaction of II, obtained by reaction of 3-methylcyclohexanone (I) and thiocarbo hydrazide, with phenacyl bromide has been studied in varying conditions leading to the formation of 6'-aryl-3-methylspiro[cyclohexane-1,3'(4'H)-[2H]thiazolo[3,2-b]-s-tetrazine] (VII). The structures II-VII have been established by elemental analysis, IR, 1H NMR and mass spectral data. The sulphur containing compounds III-VII were screened for their antimicrobial activity.