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 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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 journal › Article
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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.
UR - http://www.scopus.com/inward/record.url?scp=34250129628&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34250129628&partnerID=8YFLogxK
U2 - 10.1007/BF00515434
DO - 10.1007/BF00515434
M3 - Article
VL - 22
SP - 100
EP - 103
JO - Chemistry of Heterocyclic Compounds
JF - Chemistry of Heterocyclic Compounds
SN - 0009-3122
IS - 1
ER -