ISSN:
1042-7163
Keywords:
Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 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.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hc.520050402
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