Chemistry of Heterocyclic Compounds

, Volume 22, Issue 1, pp 100–103 | Cite as

10-Alkenylphenothiazines. 1. Synthesis and cis,trans-isomerization of 10-propenylphenothiazines

  • V. A. Anfinogenov
  • O. A. Napilkova
  • E. E. Sirotkina
  • V. D. Filimonov
  • V. D. Ogorodnikov
Article
  • 29 Downloads

Abstract

A study was carried out on the isomerization of 10-allylphenothiazine (I) in DMSO by the action of t-BuOK, KOH and NaOH. The isomerization proceeds stereospecifically at room temperature by the action of t-BuOK at an elevated temperature by the action of KOH and NaOH to give cis-10-propenylphenothiazine (II). The effect of the t-BuOK concentration, temperature and reaction time on the isomeric composition of the 10-propenylphenothiazines formed was studied. Under conditions of kinetic control, I gives II, which isomerizes under the reaction conditions to give an equilibrium mixture of cis- and trans-10-propenyl-phenothiazine with 44–45% trans isomer III. The isomerization temperature has virtually no effect on the II/III isomer ratio.

Keywords

Reaction Time DMSO Organic Chemistry Elevated Temperature Trans Isomer 

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Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • V. A. Anfinogenov
    • 1
    • 2
    • 3
  • O. A. Napilkova
    • 1
    • 2
    • 3
  • E. E. Sirotkina
    • 1
    • 2
    • 3
  • V. D. Filimonov
    • 1
    • 2
    • 3
  • V. D. Ogorodnikov
    • 1
    • 2
    • 3
  1. 1.I. I. Polzunov Altai Polytechnical InstituteBarnaul
  2. 2.Tomsk Institute of Petroleum Chemistry, Siberian DivisionAcademy of Sciences of the USSRTomsk
  3. 3.S. M. Kirov Tomsk Polytechnical InstituteTomsk

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