Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines

Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines

Treatment of N-alkyl- N-allyl-pyrrolo-2-carboxamides with catalytic amounts of palladium derivatives gave regioselectively intramolecular cyclizations to generate bicyclic pyrrolo-fused structures. Pyrrolo[1,2- a]pyrazin-1-ones were achieved in high yields by an amination reaction, while pyrrolo[2,3...

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Bibliographic Details
Published in:Tetrahedron Vol. 61; no. 5; pp. 1077 - 1082
Main Authors: Beccalli, Egle M., Broggini, Gianluigi, Martinelli, Michela, Paladino, Giuseppe
Format: Journal Article
Language:English
Published: Elsevier Ltd 31-01-2005
Subjects:
Amination
Cyclization reactions
Fused-pyrrole system
Palladium
Regioselectivity
Cyclization reactions
Fused-pyrrole system
Palladium
Amination
Regioselectivity
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Summary:Treatment of N-alkyl- N-allyl-pyrrolo-2-carboxamides with catalytic amounts of palladium derivatives gave regioselectively intramolecular cyclizations to generate bicyclic pyrrolo-fused structures. Pyrrolo[1,2- a]pyrazin-1-ones were achieved in high yields by an amination reaction, while pyrrolo[2,3- c]pyridin-7-ones and pyrrolo[3,2- c]pyridin-4-ones were obtained by an oxidative coupling process. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.11.066