Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 12, Pages 6379-6387Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00977
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- Direccion General de Investigacion del Ministerio de Economia, Ciencia e Innovacion (MICINN, Madrid DGI) [CTQ2015-67871-R]
- Gobierno Vasco, Universidad del Pais Vasco (GV) [IT 992-16]
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Both experimental and computational studies for the cycloaddition reaction between N-(3-pyridyl)aldimines and acetylenes where 1,5-naphthyridines are obtained are reported. The reaction of benzaldimine with a methoxycarbonyl group in position 2 with phenyl acetylene, styrene, and indene afforded polycyclic isoindolone derivatives. The mechanism of reaction of N-(3pyridyl)aldimines with olefins can be explained by an asynchronous [4+2] cycloaddition; in the case of acetylenes, the obtained results suggest a stepwise mechanism through a 3-azatriene.
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