Reverse-Cope cyclisations of thiahydroxylamines derived from the addition of allylic thiols to nitrones: Syntheses of 1,3-thiazolidine-N-oxides and 1,5,2-oxathiazinanes

被引:21
作者
Coogan, MP
Gravestock, MB
Knight, DW
Thornton, SR
机构
[1] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TJ,CHESHIRE,ENGLAND
[2] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(97)10244-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allylthiols 7 react as nucleophiles with nitrones 8 to give intermediate thiahydroxylamines which undergo reverse-Cope cyclisations to provide 1,3-thiazolidine-N-oxides 9; in the case of derivatives of C-phenyl nitrone, thermolysis results in smooth Meisenheimer rearrangement leading to the 1,5,2-oxathiazinane 14. (C) 1997 Elsevier Science Ltd.
引用
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页码:8549 / 8552
页数:4
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