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

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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.

Original languageEnglish
Pages (from-to)100-103
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume22
Issue number1
DOIs
Publication statusPublished - Jan 1986

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Isomerization
Isomers
Temperature
Dimethyl Sulfoxide
Kinetics
Chemical analysis

ASJC Scopus subject areas

  • Organic Chemistry

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10-Alkenylphenothiazines. 1. Synthesis and cis,trans-isomerization of 10-propenylphenothiazines. / Anfinogenov, V. A.; Napilkova, O. A.; Sirotkina, E. E.; Filimonov, V. D.; Ogorodnikov, V. D.

In: Chemistry of Heterocyclic Compounds, Vol. 22, No. 1, 01.1986, p. 100-103.

Research output: Contribution to journalArticle

Anfinogenov, V. A. ; Napilkova, O. A. ; Sirotkina, E. E. ; Filimonov, V. D. ; Ogorodnikov, V. D. / 10-Alkenylphenothiazines. 1. Synthesis and cis,trans-isomerization of 10-propenylphenothiazines. In: Chemistry of Heterocyclic Compounds. 1986 ; Vol. 22, No. 1. pp. 100-103.
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AU - Napilkova, O. A.

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AU - Filimonov, V. D.

AU - Ogorodnikov, V. D.

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