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Diazabicycloalkanes with nitrogen atoms in the nodal positions. 8. Effect of c-substituents on the N-methylation of 1,4-diazabi cyclo[2.2.2]octanes and the demethylation of their bisquaternary salts

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The introduction of substituents with various inductive constants in the 2 position of the diazabicyclo]2.2.2]octane ring gives rise to a change in the pKa values and affects the ease of introduction of a methyl group in the 1 and 4 positions, as well as the rate of demethylation of the bisquaternary salts from the 1 position. When 1,4-diazabicyclo[2.2.2]octane is treated with a sufficiently strong nucleophile, the ring is opened to give a piperazine derivative.

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, 630090, Novosibirsk

    V. I. Vysochin & G. V. Shishkin

Authors
  1. V. I. Vysochin
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  2. G. V. Shishkin
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See [1] for communication 7.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 250–255, February, 1982.

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Vysochin, V.I., Shishkin, G.V. Diazabicycloalkanes with nitrogen atoms in the nodal positions. 8. Effect of c-substituents on the N-methylation of 1,4-diazabi cyclo[2.2.2]octanes and the demethylation of their bisquaternary salts. Chem Heterocycl Compd 18, 196–201 (1982). https://doi.org/10.1007/BF00512969

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  • DOI: https://doi.org/10.1007/BF00512969

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