Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives

Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives

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 po...

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Veröffentlicht in:Journal of organic chemistry 2017-06, Vol.82 (12), p.6379-6387
Hauptverfasser: Alonso, Concepción, González, María, Palacios, Francisco, Rubiales, Gloria
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container_title Journal of organic chemistry
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creator Alonso, Concepción
González, María
Palacios, Francisco
Rubiales, Gloria
description 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-(3-pyridyl)­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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title Study of the Hetero-[4+2]-Cycloaddition Reaction of Aldimines and Alkynes. Synthesis of 1,5-Naphthyridine and Isoindolone Derivatives
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