An efficient one-pot method for the synthesis of functionalized quinolines and tetrahydronaphthyridines has been developed. The photo-Fries rearrangement of p-substituted anilides afforded differently substituted o-amino ketones that reacted in situ with acetylenic Michael acceptors such as dimethyl acetylenedicarboxylate (DMAD) to give 6,4-disubstituted quinoline 2,3-dicarboxylates. Starting from anilides derived from beta-alanine, a naphthyridine nucleus can also be assembled.
Guerrini, G., Taddei, M., Ponticelli, F. (2011). Synthesis of Functionalized Quinolines and Benzo[c][2,7]naphthyridines Based on a Photo-Fries Rearrangement. JOURNAL OF ORGANIC CHEMISTRY, 76(18), 7597-7601 [10.1021/jo201316k].
Synthesis of Functionalized Quinolines and Benzo[c][2,7]naphthyridines Based on a Photo-Fries Rearrangement
Guerrini, Giacomo;Taddei, Maurizio;Ponticelli, Fabio
2011-01-01
Abstract
An efficient one-pot method for the synthesis of functionalized quinolines and tetrahydronaphthyridines has been developed. The photo-Fries rearrangement of p-substituted anilides afforded differently substituted o-amino ketones that reacted in situ with acetylenic Michael acceptors such as dimethyl acetylenedicarboxylate (DMAD) to give 6,4-disubstituted quinoline 2,3-dicarboxylates. Starting from anilides derived from beta-alanine, a naphthyridine nucleus can also be assembled.
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https://hdl.handle.net/11365/3622
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