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Short Paper | Regular issue | Vol 83, No. 6, 2011, pp.1363-1370
Published online, 12th April, 2011
DOI: 10.3987/COM-11-12165
■ Reactions of 3,6-Bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines with Indole and 1,3,3-Trimethyl-2-methyleneindoline

Rashida I. Ishmetova, Nina K. Ignatenko, Ilya N. Ganebnykh, Svetlana G. Tolshchina, Pavel A. Slepukhin, and Gennady L. Rusinov*

*I. Ya. Postovsky Institute of Organic Synthesis of RAS, 620990, S. Kovalevskoy st, 22, Yekaterinburg, Russia

Abstract

It has been found that 3,6-bis(3,5-dimethyl-4-R-pyrazol-1-yl)-1,2,4,5-tetrazines react with indole and 1,3,3-trimethyl-2-methyleneindoline to give pyridazines as [4+2]cycloaddition products. 1,3,3-Trimethyl-2-methyleneindoline has been shown to act as C-nucleophile in the substitution of pyrazolyl group as well as in the reactions of tetrazine ring expansion in [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine derivatives.