Anionic N-Fries rearrangement of N-alkyl-2-iodo anilides induced by iodine-magnesium exchange: application for synthesis of strained 1,2,3-trisubstituted indoles |
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Authors: | Ding Fei Zhang Yongda Qu Bo Li Guisheng Farina Vittorio Lu Bruce Z Senanayake Chris H |
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Affiliation: | Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, CT 06877, USA. |
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Abstract: | A superior, mild, high-yielding one-pot process for rapid access to oxo anilides has been developed that involves three cascade reactions: iodine-magnesium exchange, regiospecific ortho N-Fries rearrangement, and in situ trapping of the formed aniline anion. Coupled with McMurry cyclization, the two-step process allows ready synthesis of strained 1,2,3-trisubstituted indoles regioselectively. |
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