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- W2025101937 abstract "Among privileged structures, indoles occupy a central place in medicinal chemistry and alkaloid research. Here we report a flexible and efficient conversion of pyrrole-3-carboxaldehydes to substituted 7-amino-5-cyanoindoles. Phosphine addition to fumaronitrile proceeds with prototropic rearrangement of the initially formed zwitterion to the thermodynamically favored phosphonium ylide, which is poised for in situ Wittig olefination. The predominantly E-alkene product positions the allylic nitrile for facile intramolecular Hoeben–Hoesch reaction in the presence of BF3·OEt2. Syntheses of 2,5- and 3,5-disubstituted 7-aminoindoles are illustrated. Additionally, dianion alkylation of the allylic nitrile is demonstrated to furnish, after cyclization, 5,6-disubstituted 7-aminoindoles to further exemplify this scalable and high-yielding method." @default.
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- W2025101937 date "2014-12-05" @default.
- W2025101937 modified "2023-10-12" @default.
- W2025101937 title "A Practical Route to Substituted 7-Aminoindoles from Pyrrole-3-carboxaldehydes" @default.
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- W2025101937 doi "https://doi.org/10.1021/ol503078h" @default.
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