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Synthesis of N-propargylanabasine derivatives by the mannich reaction

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Abstract

N-Propargylanabasine derivatives bearing various substituents at the carbon atom of the alkyne fragment were obtained by the reaction of anabasine hydrochloride with terminal alkynes and paraformaldehyde. The reaction proceeded with retention of the C(2) chiral center in anabasine fragment. The by-products of the reaction, including 1,3-diacetylene (the products of dimerization of alkynes) and conjugated vinylacetylenes (the rearrangement products of the Mannich adducts) were isolated and characterized.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. V. Mavrov & S. G. Zlotin

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  1. M. V. Mavrov
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  2. S. G. Zlotin
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Correspondence to S. G. Zlotin.

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Dedicated to Academician V. A. Tartakovsky in honor of his 75th anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1576–1585, August, 2007.

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Mavrov, M.V., Zlotin, S.G. Synthesis of N-propargylanabasine derivatives by the mannich reaction. Russ Chem Bull 56, 1637–1647 (2007). https://doi.org/10.1007/s11172-007-0256-0

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  • DOI: https://doi.org/10.1007/s11172-007-0256-0

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