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Multi-membered N-heterocyclesR 0690 Reaction of Nβ-Benzylserotonin with α,β-Unsaturated and Aryl Aldehydes in the

Presence of a Base. — The reaction of serotonin (I) with aldehydes (II), (V), (VIII), and (X) proceeds smoothly with the aid of a base to afford the corresponding azepi-noindoles. Aldehydes (IId) and (V), equipped with an α-methyl group are subject to steric hindrance. On treating (V) for 7 days, only a small amount of (VI) is isolated together with (VII). The formation of compound (VII) can be explained by the reaction of (I) with propionaldehyde, generated in situ by addition of water to aldehyde (V) and the subsequent retro-aldol step. Aldehyde (X), possessing an electron withdrawing group, only produces a moderate amount of (XI), accompanied by a small amount of β-carboline (XII). — (YAMADA, K.; NAMERIKAWA, Y.; ABE, T.; ISHIKURA*, M.; Heterocycles 77 (2009) 2, 825-828; Fac. Pharm. Sci., Health Sci. Univ. Hokkaido, Hokkaido 061, Japan; Eng.) — H. Hoennerscheid

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ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim