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

被引：29

作者：

Alonso, Concepcion ^{[1
]}

Gonzalez, Maria ^{[1
]}

Palacios, Francisco ^{[1
]}

Rubiales, Gloria ^{[1
]}

机构：

[1] Univ Basque Country, UPV EHU, Ctr Invest & Estudios Avanzados Lucio Lascaray, Dept Quim Organ 1,Fac Farm, Vitoria 01006, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 12期

关键词：

TOPOISOMERASE-I INHIBITORS; DENSITY-FUNCTIONAL THEORY; COUPLING REACTIONS; POVAROV REACTION; ALDEHYDES; TANDEM; ISOINDOLINONES; MARTINELLINE; ENERGETICS; STRATEGY;

D O I：

10.1021/acs.joc.7b00977

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6379 / 6387

页数：9

共 69 条

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