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Efficient Construction of Tri- and Tetracyclic Heterocycles from Linear 1,6-Dienes by a Domino Reaction

✍ Scribed by Yimin Hu; Fengfa Song; Fenghua Wu; Dong Cheng; Shaowu Wang

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 358 KB
Volume: 14
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200702035

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✦ Synopsis

Abstract

Tri‐ and tetracyclic heterocycle systems were constructed by a palladium‐catalyzed domino reaction of linear 1,6‐dienes that contain acryl groups with aryl halides through C–C coupling and aromatic CH functionalization. Three different acrylamides have been shown to be very active for the reaction. The substituents on the aryl halides could be ethoxycarbonyl, ketyl, chloro, sulfonyl, cyano, etc. Thus, the ready accessibility of the starting materials, the wide range of compatibility of substrates including both dienes and aryl halides, and the generality of this process make the reaction highly valuable in view of the synthetic and medicinal importance of these kinds of heterocycles.

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