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Russian Journal of Organic Chemistry

, Volume 46, Issue 5, pp 637–643 | Cite as

Synthesis and aminolysis of N-(4-chlorophenyl)- and N-(2,4-dichlorophenylsulfonyl)-N-(glycidyl)bicyclo-[2.2.1]hept-5-en-endo-ylmethylamines

  • L. I. Kas’yan
  • S. A. Prid’ma
  • V. A. Pal’chikov
  • A. O. Kas’yan
  • A. V. Turov
  • A. V. Tokar’
  • S. V. Tret’yakov
Article

Abstract

A glycidyl fragment was introduced into molecules of derivatives of bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine (sulfonamides, sulfonylurea) under the conditions of phase-transfer catalysis; carboxamides were established to be passive in this reaction; the results were compared with the calculations of the proton affinity of the nitrogen atoms in the molecules of the acyl derivatives of the framework amine. Products were obtained from reactions of N-(4-chlorophenylsulfonyl)-N-(glycidyl)bicyclo[2.2.1]hept-5-en-endo-2-ylmethylamine with benzylamine, N-benzylpiperazine, and bicyclic framework amines. The regiochemistry of the aminolysis was investiganted with the help of NMR 1H, 13C spectra, and also with the use of 2D spectra COSY, NOESY, HMQC, HMBC.

Keywords

Epoxide Ethyl Ether Glycidyl Benzylamine Epichlorohydrin 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • L. I. Kas’yan
    • 1
  • S. A. Prid’ma
    • 1
  • V. A. Pal’chikov
    • 1
  • A. O. Kas’yan
    • 2
  • A. V. Turov
    • 3
  • A. V. Tokar’
    • 1
  • S. V. Tret’yakov
    • 1
  1. 1.Oles’ Gonchar Dnepropetrovsk National UniversityDnepropetrovskUkraine
  2. 2.ProBioGen A.G.BerlinGermany
  3. 3.Shevchenko Kiev National UniversityKievUkraine

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