Synthetic approach to imidazo[1,2- a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology

N-Benzyl and ( R)- N-(α-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cycloaddition to give predominantly bridged-ring products, namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1- d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter fu...

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Bibliographic Details
Published in:Tetrahedron 2002-05, Vol.58 (22), p.4445-4450
Main Authors: Basso, Diego, Broggini, Gianluigi, Passarella, Daniele, Pilati, Tullio, Terraneo, Alberto, Zecchi, Gaetano
Format: Article
Language:English
Subjects:
imidazo[1,2- a]pyridines
intramolecular cycloaddition
nitrones
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Summary:N-Benzyl and ( R)- N-(α-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cycloaddition to give predominantly bridged-ring products, namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1- d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2- a]pyridines. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00404-0