A general route to the synthesis of 1,5-methano- and 1,5-ethano- 2,3,4,5-tetrahydro-1H-3-benzazepines.

A general approach to preparing 1,5-methano- (1) and 1,5-ethano-2,3,4,5-tetrahydro-1H-3-benzazepine (2) is discussed. This strategy involves converting an indanone or tetralone (4) to a cyanohydrin (3) which is subjected to hydrogenolysis followed by lactamization and reduction to provide bicyclic aryl piperidine (1) and bicyclic aryl homopiperidine (2).

Preparation of 1,5-methano-2,3,4,5- tetrahydro-1H-3-benzazepine via Pd-catalyzed cyclization.

[reaction: see text] A new approach to prepare 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzanepine (1) is discussed. This strategy utilized a tandem Michael addition and Pd-catalyzed cyclization to afford cyanobenzofulvene acetal 13. This indene intermediate (13) was subjected to hydrogenolysis to provide an amino ester (12) and was cyclized with base to afford lactam 5.

Quinone Alkylation Using Organocadmium Reagents: A General Synthesis of Quinols.

Reactions of p-benzoquinone with organocadmium reagents yield quinols, the result of quinone carbonyl monoalkylation. The reactions proceed in good yield and are devoid of bisaddition and hydroquinone byproducts. Quinone alkylations using this method show general applicability to p-benzoquinone as well as extended quinone systems using primary alkyl, secondary alkyl, and aryl reagents.