Preparation of some dimethylaminocyclohexa-1,3-dienes and their reactions with αβ-unsaturated ketones

Abstract

Metal-ammonia reduction of an NN-dimethylaniline usually gives the cyclohexadiene of type (1). These enamines react with ap-unsaturated ketones to give initially a 2-substituted cyclohexenone [e.g. (4)] or a hydronaphthalene ketone [e.g. (3)].

Inverse Electron‐Demanding Diels–Alder Reactions in the Chemical Synthesis of Prenylated Indole Alkaloids Containing a Bicycle[2.2.2]diazaoctane Moiety: A Theoretical Study

“…The family of prenylated indole alkaloids shows a series of interesting structural features such as bicyclo[2.2.2]diazaoctane, 2‐H pyran, spirocyclic and 2‐oxo, 3‐oxo or 3‐hydroxyindole or simple indole units [3] . After the isolation of the first member of this group in 1969, [2b] more than 300 compounds have been discovered which show a great diversity in structure and pharmacological activity, for example, stephacidins with anticancer effects, [4] taichunamides and notoamides with cytotoxic effects, [5] amoenamides with antifungal effects, [6] and brevianamides with insecticidal effects [7] (Scheme 1).…”