Synthesis of 3-and 5-amino-5-(3)-(pyrrol-2-yl)isoxazoles

被引：19
|
作者：
Sobenina, LN [1 ]
Drichkov, VN [1 ]
Mikhaleva, AI [1 ]
Petrova, OV [1 ]
Ushakov, IA [1 ]
Trofimov, BA [1 ]
机构：
[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia
来源：
TETRAHEDRON | 2005年 / 61卷 / 20期
基金：
俄罗斯基础研究基金会;
关键词：
D O I：
10.1016/j.tet.2005.03.031
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
5-Amino-3-(pyrrol-2-yl)isoxazoles were selectively prepared by the reaction of 2-(2,2-dicyano- 1-ethylthioethenyl)pyrroles with hydroxylamine in methanol. Under analogous conditions, 2-(2-carbamoyl-2-cyano-1-ethylthioethenyl) pyrroles with hydroxylamine gave 5-aminoisoxazoles and their structural isomers, 3-aminoisoxazoles (3-5% yield). The latter were selectively prepared by reacting 2-(2carbamoyl-2-cyano-1-ethylthioethenyl)pyrroles with hydroxylamine in the presence of aqueous NaOH and from the products of intramolecular cyclization of 2-(2-carbamoyl-2-cyano- I -ethylthioethenyl)pyrroles,1-ethylthio-3-iminopyrrolizines and hydroxylamine. © 2005 Published by Elsevier Ltd.
引用
收藏
页码：4841 / 4849
页数：9
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