ChemInform 2009, 40, issue 01 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.cheminform.wiley-vch.de Multi-membered N-heterocycles R 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 27- 166

ChemInform Abstract: Reaction of Nβ-Benzylserotonin with α,β-Unsaturated and Aryl Aldehydes in the Presence of a Base

Download PDF Report

Upload
koji-yamada
View
216
Download
2

Embed Size (px)

Citation preview

Page 1: ChemInform Abstract: Reaction of Nβ-Benzylserotonin with α,β-Unsaturated and Aryl Aldehydes in the Presence of a Base

www.cheminform.wiley-vch.de

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

27- 166