Vinylic nucleophilic substitution in functionalized 2-vinylpyrroles: a route to a new family of stable enols

被引：6
作者：
Trofimov, BA
Petrova, OV
Sobenina, LN
Drichkov, VN
Mikhaleva, AI
Ushakov, IA
Tarasova, OA
Kazheva, ON
Chekhlov, AN
Dyachenko, OA
机构：
[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia
[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia
来源：
TETRAHEDRON | 2006年 / 62卷 / 17期
关键词：
2-vinylpyrroles; 3-iminopyrrolizines; vinylic nucleophilic substitution;
D O I：
10.1016/j.tet.2006.02.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-(2-Cyano-1-ethylthioethenyl)pyrroles easy exchange their ethylthio group for hydroxyl (NaOH, H2O-methanol. 40-45 degrees C, I h) to give 2-(2-cyano-1-hydroxyethenyl)pyrroles, a new family of stable enols, in 50-94% yields. The vinylic nucleophilic substitution proceeds at the double bond of both the starting pyrroles and their cyclic isomers, 3-iminopyrrolizines. X-ray structure analysis and NMR spectra show the enols to be stabilized by exceptionally strong intramolecular H-bonding (c) 2006 Elsevier Ltd. All rights reserved.
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页码：4146 / 4152
页数：7
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