Synthesis of 3-and 5-amino-5-(3)-(pyrrol-2-yl)isoxazoles
Synthesis of 3-and 5-amino-5-(3)-(pyrrol-2-yl)isoxazoles
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DOI：
10.1016/j.tet.2005.03.031
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发表时间：
2005-05-16
期刊：
影响因子：
2.1
通讯作者：
Trofimov, BA
中科院分区：
文献类型：
--
作者：
Sobenina, LN;Drichkov, VN;Trofimov, BA
以2-（2，2-二氰基-1-乙硫基）吡咯为原料，在甲醇中与羟胺反应，选择性地合成了5-氨基-3-（吡咯-2-基）异恶唑。在类似条件下，2-（2-氨基甲酰基-2-氰基-1-乙硫基）吡咯与羟胺反应，得到5-氨基异恶唑及其结构异构体3-氨基异恶唑（产率3-5%）。后者是由2-（2-氨甲酰基-2-氰基-1-乙硫基）吡咯与羟胺在NaOH水溶液中反应，并由2-（2-氨甲酰基-2-氰基-1-乙硫基）吡咯、1-乙硫基-3-亚氨基吡咯里嗪和羟胺的分子内环化产物选择性地制备的。© 2005由Elsevier Ltd.出版。
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.