2-Allyl- N-benzyl substituted α-naphthylamines as building blocks in heterocyclic synthesis. New and efficient syntheses of benz[ e]naphtho[1,2- b]azepine and naphtho[1,2- b]azepine derivatives

A new series of 13-acetyl-7,12-dihydro-7-ethylbenz[ e]naphtho[1,2- b]azepine ( 4a– d) and 2-aryl-4-hydroxy-2,3,4,5-tetrahydronaphtho[1,2- b]azepine derivatives ( 6a– d) have been synthesized from N-allyl- N-benzyl substituted α-naphthylamines ( 1a– d) by utilizing aromatic amino-Claisen rearrangemen...

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Bibliographic Details
Published in:Tetrahedron letters 2006-08, Vol.47 (32), p.5825-5828
Main Authors: Yépez, Andrés Felipe, Palma, Alirio, Stashenko, Elena, Bahsas, Ali, Amaro-Luis, Juan M.
Format: Article
Language:English
Subjects:
Amino-Claisen rearrangement
Benz[ e]naphtho[1,2- b]azepines
Intramolecular dipolar 1,3-cycloaddition
Intramolecular Friedel–Crafts alkylation
Tetrahydronaphtho[1,2- b]azepines
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Summary:A new series of 13-acetyl-7,12-dihydro-7-ethylbenz[ e]naphtho[1,2- b]azepine ( 4a– d) and 2-aryl-4-hydroxy-2,3,4,5-tetrahydronaphtho[1,2- b]azepine derivatives ( 6a– d) have been synthesized from N-allyl- N-benzyl substituted α-naphthylamines ( 1a– d) by utilizing aromatic amino-Claisen rearrangement, intramolecular Friedel–Crafts alkylation and intramolecular dipolar 1,3-cycloaddition nitrone-olefin reactions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.04.160