Valentina I. Gulevskava,, A. Kuvshinov, Svyatoslav A.Shevelev,
2001
Citations
0
Influential Citations
4
Citations
Journal
Heterocyclic Communications
Abstract
Interaction of C-(2,4,6-trinitrophenyl)-N-arylazomethines (1) with methyl thioglycolate (2) in the presence of K2CO3 in MeCN resulted in the orthoN02 group substitution in 1 by the SCH2CC>2Me fragment. Thus obtained sulfides 3 undergo intramolecular cyclisation with the further in situ dehydrogenation of the cyclisation product to form previously unknown methyl 3-arylamino-4,6-dinitrobenzo[b]thiophene-2-carboxylates. In the case of C(2,4,6-trinitrophenyl)-N-hetarylazomethines (hetaryl=1,3,5-pyrazolyl-4, thiazolyl2), under the same conditions, we observed the elimination of a hetarylamine. Dehydrogenation in this case either did not occur at all or proceeded in very low yield.