Abstract
AbstractThe reaction of 3‐mercapto‐4‐arylideneamino‐1,2,4‐triazoles 2b‐d, 3a‐d with ethyl bromoacetate and/or phenacyl bromide in hot DMF and triethylamine affords the stereochemically pure 7‐acyl‐6‐aryl‐6,7‐dihydro‐5H‐1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazines 4b‐d, 5a‐d, 6b,d in which the consecutive hydrogen atoms N(5)H‐C(6)H‐C(7)H are cis to each other. This stereochemistry was determined by 1H NMR spectroscopy and confirmed by comparison with the spectrum of 3,6‐diphenyl‐6,7‐dihydro‐5H‐1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazine 10. The latter was prepared by NaBH4 reduction of 3,6‐diphenyl‐5H‐1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazine 9. The reported reactions offer two interesting stereospecific syntheses of the condensed heterocyclic compounds.
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