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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 11, pp 1455–1459 | Cite as

The Mannich reaction in the synthesis of N,S-containing heterocycles. 7. Effective one-pot synthesis of derivatives of spiro[3,5,7,11-tetraazatricyclo-[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]

  • V. V. Dotsenko
  • S. G. KrivokolyskoEmail author
  • V. P. Litvinov
Article

Abstract

5,11-Disubstituted derivatives of 1′-isopropyl-8-thioxospiro[3,5,7,11-tetrazatricyclo[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]-1,9-dicar bonitrile was obtained by the interaction of 10-amino-9-aza-3-azonia-7,11-dicyano-3-isopropylspiro[5,5]undeca-7,10-diene-8-thiolate with 2 equiv. of a primary amine and excess of formaldehyde. An anomalous reaction product was obtained with o-toluidine — 7,9-dicyano-1′-isopropyl-3-(2-methylphenyl)-1,2,3,4-tetrahydrospiro[pyrido[1,2-a][1,3,5]triazine-8,4′-piper idinium]-6-thiolate.

Keywords

10-amino-9-aza-3-azonia-7,11-dicyano-3-isopropylspiro[5,5]undeca-7,1-diene-8-thiolate pyridine-2-thiolates spiro[3,5,7,11]-tetraazatricyclo[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]-1,9-dicarbonitrile aminomethylation the Mannich reaction cyclocondensation 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • V. V. Dotsenko
    • 1
  • S. G. Krivokolysko
    • 1
    Email author
  • V. P. Litvinov
    • 2
  1. 1.“ChemEx” LaboratoryVladimir Dal East-Ukrainian National UniversityLuganskUkraine
  2. 2.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscow

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