Efficient sulfonation of 1-phenylsulfonyl-1H-pyrroles and 1-phenylsulfonyl-1H-indoles using chlorosulfonic acid in acetonitrile
2006 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 62, no 8, 1699-1707 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2006. Vol. 62, no 8, 1699-1707 p.
IdentifiersURN: urn:nbn:se:sh:diva-14306DOI: 10.1016/j.tet.2005.11.062ISI: 000235414100005ScopusID: 2-s2.0-31444435552OAI: oai:DiVA.org:sh-14306DiVA: diva2:468134