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
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 49期
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
收藏
页码：8549 / 8552
页数：4
相关论文
共 16 条
[1]  
ALBINI A, 1993, SYNTHESIS-STUTTGART, P263
[2]  
ASCHERL B, 1987, B SOC CHIM BELG, V96, P51
[3]   Factors influencing the reverse-Cope approach to 1,2,5-oxadiazinanes from allylamines and nitrones: Optimization of a new vicinal diamine synthesis [J].
Bell, KE ;
Coogan, MP ;
Gravestock, MB ;
Knight, DW ;
Thornton, SR .
TETRAHEDRON LETTERS, 1997, 38 (49) :8545-8548
[4]   NITRONES AND OXAZIRIDINES .22. PREPARATION AND CYCLIZATION OF SOME DELTA,EPSILON-UNSATURATED HYDROXYLAMINES [J].
BLACK, DSC ;
DOYLE, JE .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (10) :2317-2322
[5]   [4+2]-CYCLOADDITIONS OF THIONES WITH NITROSOALKENES - SYNTHESIS OF DERIVATIVES OF 4H-1,5,2-OXATHIAZINE, A NEW HETEROCYCLIC SYSTEM [J].
BONINI, BF ;
FORESTI, E ;
MACCAGNANI, G ;
MAZZANTI, G ;
SABATINO, P ;
ZANI, P .
TETRAHEDRON LETTERS, 1985, 26 (17) :2131-2134
[6]   REVERSE COPE ELIMINATION-REACTIONS .1. MECHANISM AND SCOPE [J].
CIGANEK, E ;
READ, JM ;
CALABRESE, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5795-5802
[7]   REVERSE COPE ELIMINATION-REACTIONS .2. APPLICATION TO SYNTHESIS(1) [J].
CIGANEK, E .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5803-5807
[8]   N-alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines .8. the scope of tandem reactions involving hydroxylamine-alkyne cyclisations [J].
Davison, EC ;
Forbes, IT ;
Holmes, AB ;
Warner, JA .
TETRAHEDRON, 1996, 52 (35) :11601-11624
[9]  
DONDONI A, 1996, COMP HETEROCYCLIC 2, V3, P402
[10]   RETRO-COPE ELIMINATIONS IN THE SYNTHESIS OF 1,2,5-OXADIAZINANES FROM ALLYLAMINES AND NITRONES - A METHOD FOR THE AMINATION OF UNACTIVATED ALKENES [J].
GRAVESTOCK, MB ;
KNIGHT, DW ;
THORNTON, SR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :169-171
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