N-hetarylethylenes. 1. Synthesis and isomerization of 10-allyland 10-propenylphenoxazines

V. A. Anfinogenov, Andrey Ivanovich Khlebnikov, V. D. Filimonov, V. D. Ogorodnikov

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Abstract

Alkylation of phenoxazine with allyl bromide has given 10-allylphenoxazine. The prototropic isomerization of 10-allylphenoxazine in DMSO on treatment with t-BuOK, KOH, and NaOH has been examined. At elevated temperatures, mixtures of cis- and trans-10-propenylphenoxazines are formed, but at room temperature in the presence of t-BuOK isomerization proceeds stereoselectively to give cis-10-propenylphenoxazine. The influence of temperature and reaction times on the isomeric composition of the 10-propenylphenoxazines has been studied. The cis-propenylphenoxazine obtained in the kinetically controlled reaction isomerizes under the reaction conditions to the equilibrium mixture of cis- and transisomers of 10-propenylphenoxazine.

Original languageEnglish
Pages (from-to)1384-1387
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume24
Issue number12
DOIs
Publication statusPublished - Dec 1988

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Isomerization
Alkylation
Dimethyl Sulfoxide
Temperature
Chemical analysis

ASJC Scopus subject areas

  • Organic Chemistry

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N-hetarylethylenes. 1. Synthesis and isomerization of 10-allyland 10-propenylphenoxazines. / Anfinogenov, V. A.; Khlebnikov, Andrey Ivanovich; Filimonov, V. D.; Ogorodnikov, V. D.

In: Chemistry of Heterocyclic Compounds, Vol. 24, No. 12, 12.1988, p. 1384-1387.

Research output: Contribution to journalArticle

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