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 a...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-08, Vol.69 (17), p.5756-5759
Main Authors: O'Donnell, Christopher J, Singer, Robert A, Brubaker, Jason D, McKinley, Jason D
Format: Article
Language:English
Subjects:
Benzazepines - chemical synthesis
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Indans - chemistry
Indicators and Reagents
Molecular Structure
Nitriles - chemistry
Organic chemistry
Preparations and properties
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Summary: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).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049122q