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Reaction of the N-mesylates of 1,3a,4,8b-tetrahydrocyclopenta[b]indoles and 3,4,4a,9a-tetrahydrocarbazoles with dimethyldioxirane and bromine

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In reaction with dimethyldioxirane N-mesyl-1,3a,4,8b-tetrahydrocyclopenta[b]indoles and N-mesyl-3,3,4a,9a-tetrahydrocarbazoles mostly form the trans-epoxide. The reaction with molecular bromine leads to the product from halogenation in the aromatic ring, i.e., the corresponding N-mesyl-7-bromo-1,3a,4,8b-tetrahydrocyclopenta[b]indole or N-mesyl-6-bromo-3,4,4a,9a-tetrahydrocarbazole.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1306–1313, September, 2006.

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Gataullin, R.R., Ishberdina, R.R., Antipin, A.V. et al. Reaction of the N-mesylates of 1,3a,4,8b-tetrahydrocyclopenta[b]indoles and 3,4,4a,9a-tetrahydrocarbazoles with dimethyldioxirane and bromine. Chem Heterocycl Compd 42, 1130–1136 (2006). https://doi.org/10.1007/s10593-006-0216-x

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  • DOI: https://doi.org/10.1007/s10593-006-0216-x

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