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Synthesis of bridged heterocycles from cis-pyrrolidine-2,4-dicarboxylic acids: I. 3,6-Diazabicyclo[3.2.1]octanes

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Abstract

cis-5-Arylpyrrolidine-2,4-dicarboxylic acid monoamides undergo thermal intramolecular condensation with formation of bicyclic imides having a 3,6-diazabicyclo[3.2.1]octane skeleton. The use of copper(I) cyanide as catalyst ensures high yields of 3,6-diazabicyclo[3.2.1]octane-2,4-diones substituted at the 3-, 5-, 6-, and 7-positions. (1R*,5R*,7S*)-7-(4-Chlorophenyl)-5,6-dimethyl-3,6-diazabicyclo[3.2.1]octane-2,4-dione was found to inhibit thrombin in a buffer solution at a millimolar concentration.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    K. V. Kudryavtsev

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  1. K. V. Kudryavtsev
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Correspondence to K. V. Kudryavtsev.

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Original Russian Text © K.V. Kudryavtsev, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 3, pp. 379–386.

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Kudryavtsev, K.V. Synthesis of bridged heterocycles from cis-pyrrolidine-2,4-dicarboxylic acids: I. 3,6-Diazabicyclo[3.2.1]octanes. Russ J Org Chem 46, 372–379 (2010). https://doi.org/10.1134/S1070428010030127

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  • DOI: https://doi.org/10.1134/S1070428010030127

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