Multi-membered N-heterocycles R 0690Reaction 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 azepinoindoles. 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
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.