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

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 language	English
Pages (from-to)	100-103
Number of pages	4
Journal	Chemistry of Heterocyclic Compounds
Volume	22
Issue number	1
DOIs	https://doi.org/10.1007/BF00515434
Publication status	Published - Jan 1986

ASJC Scopus subject areas

Organic Chemistry

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@article{dcfbd91d4cf446ee95f557b6cf502c9d,

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

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.",

author = "Anfinogenov, {V. A.} and Napilkova, {O. A.} and Sirotkina, {E. E.} and Filimonov, {V. D.} and Ogorodnikov, {V. D.}",

year = "1986",

month = jan,

doi = "10.1007/BF00515434",

language = "English",

volume = "22",

pages = "100--103",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer New York",

number = "1",

}

TY - JOUR

T1 - 10-Alkenylphenothiazines. 1. Synthesis and cis,trans-isomerization of 10-propenylphenothiazines

AU - Anfinogenov, V. A.

AU - Napilkova, O. A.

AU - Sirotkina, E. E.

AU - Filimonov, V. D.

AU - Ogorodnikov, V. D.

PY - 1986/1

Y1 - 1986/1

N2 - 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.

AB - 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.

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