Synthesis of sultams by cycloalkylation of (alkoxycarbonylmethane)sulfonanilides |
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Authors: | V A Rassadin A A Tomashevskii V V Sokolov A A Potekhin |
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Institution: | (1) Saint Petersburg University, Saint Petersburg, 198504, Russia |
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Abstract: | (Methoxycarbonylmethane)sulfonanilides are alkylated by α, ω-dihaloalkanes in K2CO3-DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of
substituents in the aromatic nucleus, although substituents in the ortho position do not obstruct the reaction and in the
case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives
of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 605–617, April, 2008. |
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Keywords: | (methoxycarbonylmethane)sulfonanilides sultams cyclopropanes heterocyclization |
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