Synthesis of azepino[3,4b]indoles via the Plancher rearrangement |
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Authors: | Shane A Eisenbeis James R Phillips Diane Rescek Yatsandra Oyola-Cintron |
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Institution: | Pfizer Research and Development, Eastern Point Road, Groton, CT 06340, USA |
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Abstract: | The reaction of benzyl 3-formylpiperidine-1-carboxylate and aryl hydrazines under standard Fisher Indole conditions followed by reductive work-up affords azepino3,4b]indoles in moderate to good yields. The products are proposed to be derived via a Plancher rearrangement (a) Plancher, G. Gazz. Chim. Ital. 1898, 28, II, 374; (b) Plancher, G. Atti. Accad.Lincei1900, 9, 5, 115; (c) Boyd-Barrett, H. S. J. Chem. Soc.1932, 321]. |
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Keywords: | Azepino[3 4b]indoles Fisher indole Plancher rearrangement |
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