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.
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G. N. Kurov, L. I. Svyatkina, E. G. Pal'chuk, I. P. Naumova, and G. G. Skvortsova, Zh. Obshch. Khim., 54, 178 (1984).
V. K. Turchaninov, A. G. Gorshkov, M. F. Larin, and G. G. Skvortsov, Vysokomol. Soedin., 25A, 1892 (1983).
G. G. Skvortsova, M. F. Shostakovskii, and G. N. Kurov, Zh. Org. Khim., 8, 382 (1972).
P. Charpentier, Comptes Rendus, 225, 306 (1947).
M. Julia, A. Schouteeten, and M. Bailerge, Tetrah. Lett., No. 38, 3433 (1974).
T. Sauer and H. Prahl, Chem. Ber., 102, 1917 (1969).
V. D. Filimonov, S. G. Gorbachev, and E. E. Sirotkina, Khim. Geterotsikl. Soedin., No. 3, 340 (1980).
I. I. H. McDowell, Acta Crystogr., B32, 5 (1976).
G. Fronsa, R. Mondelli, and G. Scapini, J. Magn. Reson., 23, 437 (1976).
D. Simov, L. Kamenov, and S. Stoyanov, Khim. Geterotsikl. Soedin., No. 4, 497 (1973).
V. D. Filimonov, V. A. Anfinogenov, and S. G. Gorbachev, Khim. Geterotsikl. Soedin., No. 12, 1640 (1982).
J. Huet, Tetrahedron, 34, 2473 (1978).
E. Tasinen and P. Liukas, Acta Chem. Scand., 28, 114 (1974).
V. A. Rodionov and V. D. Filimonov, Zh. Org. Khim., 18, 1094 (1982).
N. D. Epiotis, D. Bjorkquist, L. Bjorkquist, and S. Sarkanen, J. Am. Chem. Soc., 95, 7558 (1973).
D. Simov and L. Kamenov, Godishnik Sof. Univ., 60, 247 (1965/66).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 121–124, January, 1986.
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Anfinogenov, V.A., Napilkova, O.A., Sirotkina, E.E. et al. 10-Alkenylphenothiazines. 1. Synthesis and cis,trans-isomerization of 10-propenylphenothiazines. Chem Heterocycl Compd 22, 100–103 (1986). https://doi.org/10.1007/BF00515434
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DOI: https://doi.org/10.1007/BF00515434