Facile preparation of indoles and 1,2-benzothiazine 1,1-dioxides: nucleophilic addition of sulfonamides to bromoacetylenes and subsequent palladium-catalyzed cyclization |
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Authors: | Yamagishi Masahito Nishigai Ken Ishii Azusa Hata Takeshi Urabe Hirokazu |
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Affiliation: | Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan. |
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Abstract: | Bromine as a double agent: The bromine atom in 1-bromo-1-alkynes works as an electron-withdrawing group to effect the nucleophilic addition of sulfonamides. It again plays a pivotal role in the palladium-catalyzed cyclization of the resultant (Z)-2-(sulfonylamino)-1-bromoalkenes into nitrogen heterocycles (see scheme). |
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Keywords: | alkynes cyclizations indoles nucleophilic addition palladium |
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