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Diazabicycloalkanes with nitrogen atoms in bridgehead positions 20. Synthesis of naphtho[2,3-b]-1,4-diazabicyclo[2.2.2]octene

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reaction of 2-acetamido-3-bis(2-hydroxyethyl)aminonaphthalene with phosphorus oxychloride leads to the formation of 2-methyl-1-(2-chloroethyl)naphtho[2,3-d]imidazole, while reaction with hydrobromic acid gives naphtho[23-b]-1,4-diozabicyclo[2.2.2]octane in 13% yield. The yield of the latter can be increased to 45% by exchange of the hydroxyl groups in the starting material by chlorine and by deacetylation.

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For Communication 19, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 97–100, January, 1991.

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Kuznetsova, E.N., Shishkin, G.C. Diazabicycloalkanes with nitrogen atoms in bridgehead positions 20. Synthesis of naphtho[2,3-b]-1,4-diazabicyclo[2.2.2]octene. Chem Heterocycl Compd 27, 80–83 (1991). https://doi.org/10.1007/BF00633224

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  • DOI: https://doi.org/10.1007/BF00633224

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