Regioselective N-vinylation of cyclic thionocarbamates through a vinyl bis-sulfone methodology

被引：17
作者：
Girniene, J
Tardy, S
Tatibouët, A
Sackus, A
Rollin, P
机构：
[1] Univ Orleans, ICOA, UMR 6005, F-45067 Orleans, France
[2] Kaunas Univ Technol, Dept Organ Chem, LT-3028 Kaunas, Lithuania
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 34期
关键词：
oxazolidinethione; oxazinethione; carbohydrate; BPSE; N-vinylation;
D O I：
10.1016/j.tetlet.2004.06.124
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A vinyl bis-sulfone Michael type approach towards heteroatom vinylation was applied on nitrogen derivatives. Cyclic thionocarbamates-mainly 1,3-oxazolidine-2-thiones-were converted into their N-vinyl counterparts; the procedure proved particularly efficient in the case of carbohydrate-derived complex structures. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码：6443 / 6446
页数：4
相关论文
共 35 条
[1]  
ABELE E, 2002, HETEROCYCL COMPD, V38, P682
[2]   Synthesis of vinyl monomers with active azaaromatic groups. Phase-transfer catalytic approach. [J].
Bogdal, D ;
Jaskot, K .
SYNTHETIC COMMUNICATIONS, 2000, 30 (18) :3341-3352
[3]   Formation of enamides via palladium(II)-catalyzed vinyl transfer from vinyl ethers to nitrogen nucleophiles [J].
Brice, JL ;
Meerdink, JE ;
Stahl, SS .
ORGANIC LETTERS, 2004, 6 (11) :1845-1848
[4]   A general, selective synthesis of ω-hydroxyethenyl ethers [J].
Cabianca, E ;
Chéry, F ;
Rollin, P ;
Tatibouët, A ;
De Lucchi, O .
TETRAHEDRON LETTERS, 2002, 43 (04) :585-587
[5]   Investigating thio-analogues of PSE acetals:: a more complex reaction [J].
Cabianca, E ;
Tatibouët, A ;
Chéry, F ;
Pillard, C ;
De Lucchi, O ;
Rollin, P .
TETRAHEDRON LETTERS, 2003, 44 (30) :5723-5725
[6]  
Cabianca E, 2001, SYNLETT, P1962
[7]   Synthesis of sugar-based ethenyl ethers through a vinyl bis-sulfone methodology [J].
Chéry, F ;
Desroses, M ;
Tatibouët, A ;
De Lucchi, O ;
Rollin, P .
TETRAHEDRON, 2003, 59 (25) :4563-4572
[8]  
Chéry F, 2001, SYNTHESIS-STUTTGART, P286
[9]   Phenylsulfonylethylidene (PSE) acetals as atypical carbohydrate-protective groups [J].
Chéry, F ;
Rollin, P ;
De Lucchi, O ;
Cossu, S .
TETRAHEDRON LETTERS, 2000, 41 (14) :2357-2360
[10]   A simple preparation of N-vinyl derivatives of DNA nucleobases. [J].
Ciapetti, P ;
Taddei, M .
TETRAHEDRON, 1998, 54 (37) :11305-11310
1234