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Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile |
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| Authors: | Tomasz Janosik Hamid Shirani Ilham Malky Jan Bergman |
| Affiliation: | a Unit for Organic Chemistry, CNT, Department of Biosciences at Novum, Karolinska Institute, Novum Research Park, SE-141 57, Huddinge, Sweden b Preformulation and Biopharmaceutics, Solid State Analysis AstraZeneca PAR & D/SBBG B341:3, SE-151 85 Södertälje, Sweden c Södertörn University College, SE-141 04 Huddinge, Sweden |
| Abstract: | 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. |
| Keywords: | Pyrroles Indoles Sulfonation Chlorosulfonic acid |
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