Issue 0, 1987
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of 6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines by a C–C ring cyclization under mild conditions

Pedro Molina,   Mateo Alajarín,   Ma. Jesús Pérez de Veg,   Ma. de la Concepción Foces-Foces,   Felix Hernández Cano,   Rosa Ma. Claramunt  and  José Elguero  

Abstract

The reaction between Schiff bases derived from 4-amino-2-methyl-5-methylthio-2H-1,2,4-triazole-3(4H)-thione and phenacyl bromides yields 7-aroyl-6-aryl-6,7-dihydro-1-methyl-3-methylthio-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazinium bromides [(6)–(11)].The structure of one of these compounds, (6)(in which both aryl groups are phenyl), has been determined by X-ray crystallography. It incorporates dioxane molecules and the bromide ion is sandwiched between two units. In the 1,3,4-thiadiazinium ring the consecutive hydrogen atoms –N(5)H–C(6)H–C(7)H– are trans to each other, the ring showing an EC6 conformation. The crystalline trans derivatives equilibrate to a 60:40 mixture of trans and cis 7-aroyl-6-aryl isomers, which have been analysed by 1H and 13C n.m.r. spectroscopy.

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Article information

DOI
https://doi.org/10.1039/P19870001853
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1987, 1853-1860

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Synthesis of 6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines by a C–C ring cyclization under mild conditions

P. Molina, M. Alajarín, Ma. J. P. de Veg, Ma. de la Concepción Foces-Foces, F. H. Cano, R. Ma. Claramunt and J. Elguero, J. Chem. Soc., Perkin Trans. 1, 1987, 1853 DOI: 10.1039/P19870001853

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