A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane
- 作者：Lyudmila V. Saloutina ; Aleks ; r Ya. Zapevalov ; Victor I. Saloutin ; Pavel A. Slepukhin ; Mikhail I. Kodess ; Valentina E. Kirichenko ; Marina G. Pervova ; Oleg N. Chupakhin
- 刊名：Journal of Fluorine Chemistry
- 出版年：2007
- 期刊代码：52_00221139
- 类别：ch
- 出版时间：July 2007
- 卷：128
- 期：7
- 页码：769-778
- 文件大小：575 K
摘要
The reaction of octafluoro-2,3-epoxybutane 1 with 2-aminothiophenol gave three kinds of novel fluorocontaining N,S-heterocyclic compounds depending on the solvent nature: 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol 2, 2-trifluoromethyl-2-[1-(2-aminophenylthio)-2,2,2-trifluoroethyl]-1,3-benzothiazolidine 6 and 5a,11a-bis(trifluoromethyl)-5a,6,11a,12-tetrahydro-5,11-dithia-6,12-diazanaphthacene 5. Use of the toluene, dioxane, tetrahydrofuran, acetonitrile and dimethoxyethane gave the unexpected dihydrobenzothiazine 2 (RS,SR > RR,SS) in good to moderate yields. In dimethylsulfoxide and N,N-dimethylacetamide, unusual cyclization occurred resulting in benzothiazolidine 6 (RS,SR/RR,SS 1:1) in moderate yields. Formation of minor 1,1,1,3,4,4,4-heptafluoro-3-(2-aminophenylthio)-2,2-dihydroxybutane 4 which was converted into bis(benzothiazine) 5 was observed in all solvents tested with the exception of toluene and dioxane. The molecular structure of the RS,SR-diastereomer of dihydrobenzothiazine 2, bis(benzothiazine) 5 and the RS,SR-diastereomer of benzothiazolidine 6 has been established by X-ray crystallography.