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Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
Tetrahedron ( IF 2.1 ) Pub Date : 20 February 2006 , DOI: 10.1016/j.tet.2005.11.062
Tomasz Janosik , Hamid Shirani , Niklas Wahlström , Ilham Malky , Birgitta Stensland , Jan Bergman

The sulfonation of various 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile has been studied, leading to the development of a clean and operationally simple protocol allowing direct synthesis of the corresponding 1-phenylsulfonyl-1H-pyrrole-3-sulfonyl chlorides and 1-phenylsulfonyl-1H-indole-3-sulfonyl chlorides, respectively, both of which may be easily converted to various sulfonamide derivatives by treatment with nitrogen nucleophiles. Efficient and selective removal of the phenylsulfonyl- or tosyl groups in the sulfonamide series may be achieved under mild conditions.

中文翻译:

使用氯磺酸在乙腈中对1-苯基磺酰基-1 H-吡咯和1-苯基磺酰基-1 H-吲哚进行高效磺化

已经研究了使用氯磺酸在乙腈中磺化各种1-苯基磺酰基-1 H-吡咯和1-苯基磺酰基-1 H-吲哚的方法,从而开发了一种清洁,操作简单的方法,可以直接合成相应的1-苯基磺酰基-1 H-吡咯-3-磺酰氯和1-苯基磺酰基-1 H-吲哚-3-磺酰氯,通过用氮亲核试剂处理,它们都可以容易地转化为各种磺酰胺衍生物。在温和的条件下可以有效和选择性地除去磺酰胺系列中的苯磺酰基或甲苯磺酰基。
更新日期:2017-01-31
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