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

页码：8549 / 8552

页数：4

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
Bell, KE
Coogan, MP
Gravestock, MB
Knight, DW
Thornton, SR
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8545 - 8548
[4] NITRONES AND OXAZIRIDINES .22. PREPARATION AND CYCLIZATION OF SOME DELTA,EPSILON-UNSATURATED HYDROXYLAMINES
BLACK, DSC
DOYLE, JE
[J]. 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
BONINI, BF
FORESTI, E
MACCAGNANI, G
MAZZANTI, G
SABATINO, P
ZANI, P
[J]. TETRAHEDRON LETTERS, 1985, 26 (17) : 2131 - 2134
[6] REVERSE COPE ELIMINATION-REACTIONS .1. MECHANISM AND SCOPE
CIGANEK, E
READ, JM
CALABRESE, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) : 5795 - 5802
[7] REVERSE COPE ELIMINATION-REACTIONS .2. APPLICATION TO SYNTHESIS(1)
CIGANEK, E
[J]. 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
Davison, EC
Forbes, IT
Holmes, AB
Warner, JA
[J]. 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
GRAVESTOCK, MB
KNIGHT, DW
THORNTON, SR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) : 169 - 171

← 1 2 →