Synthesis of Tricyclic Quinolones and Naphthyridones by Intramolecular Heck Cyclization of Functionalized Electron-Rich Heterocycles

Starting from commercially available pyrrole‐ and thiophene‐2‐carboxylic acids 1 or thiophene‐ and furan‐3‐carboxylic acids 6, we report the synthesis of tricyclic fused quinolone and naphthyridone derivatives, in only three steps, by an intramolecular Heck cyclization. We also report the use of mic...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2005-05, Vol.2005 (10), p.2091-2096
Main Authors: Beccalli, Egle M., Broggini, Gianluigi, Martinelli, Michela, Paladino, Giuseppe, Zoni, Caterina
Format: Article
Language:English
Subjects:
Cyclization
Heck reaction
Lactam
Microwaves
Palladium
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Summary:Starting from commercially available pyrrole‐ and thiophene‐2‐carboxylic acids 1 or thiophene‐ and furan‐3‐carboxylic acids 6, we report the synthesis of tricyclic fused quinolone and naphthyridone derivatives, in only three steps, by an intramolecular Heck cyclization. We also report the use of microwave irradiation to obtain, in some cases, better yields of cyclized products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200400817