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Chemistry of Heterocyclic Compounds

, Volume 45, Issue 2, pp 188–193 | Cite as

Synthesis of 1,2,3,4-tetrahydropyrido- [2,3-b]pyrazine-2,3-dione derivatives with a chiral substituent at the nitrogen atom

  • A. V. Kurkin
  • K. V. Bukhryakov
  • M. A. YurovskayaEmail author
Article

The sequence of steps including nucleophilic substitution of the chlorine atom in 2-chloro-3-nitropyridine by esters of optically active phenylalanine, reduction of the nitro group, acylation with ethyl oxalyl chloride, and intramolecular cyclization, leads to the synthesis of derivatives of 1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-2,3-dione with a chiral substituent at the nitrogen atom. It was established that, depending on the conditions of carrying out the cyclization, the parallel formation of derivatives of imidazo[4,5-b]pyridine is possible. Conditions were found for selectively carrying out the cyclization under with only structures of pyrazines or imidazole condensed with pyridine were formed.

Keywords

tert-butyl ester of imidazo-[4,5-b]pyridine-2-carboxylic acid 2-chloro-3-nitropyridine, 1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-2,3-diones chiral substituent at the nitrogen atom esters of optically active phenylalanine nucleophilic substitution 

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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • A. V. Kurkin
    • 1
  • K. V. Bukhryakov
    • 1
  • M. A. Yurovskaya
    • 1
    Email author
  1. 1.M. V. Lomonosov Moscow State UniversityMoscowRussia

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