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 | |
| Publication status | Published - Jan 1986 |
ASJC Scopus subject areas
- Organic Chemistry
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Anfinogenov, V. A., Napilkova, O. A., Sirotkina, E. E., Filimonov, V. D., & Ogorodnikov, V. D. (1986). 10-Alkenylphenothiazines. 1. Synthesis and cis,trans-isomerization of 10-propenylphenothiazines. Chemistry of Heterocyclic Compounds, 22(1), 100-103. https://doi.org/10.1007/BF00515434