Synthesis of Functionalized Quinolines and Benzo[c][2,7]naphthyridines Based on a Photo-Fries Rearrangement

Autor:	Giacomo Guerrini, Maurizio Taddei, Fabio Ponticelli
Rok vydání:	2011
Předmět:	Dimethyl acetylenedicarboxylate chemistry.chemical_compound Fries rearrangement Chemistry Organic Chemistry Quinoline Organic chemistry
Zdroj:	The Journal of Organic Chemistry. 76:7597-7601
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo201316k
Popis:	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 β-alanine, a naphthyridine nucleus can also be assembled.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a823bed7af3ef12010ecd7b9d76ecf5d https://doi.org/10.1021/jo201316k Zobrazit plný text záznamu