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J Org Chem. 2014 Aug 01;79(15):7232-8. doi: 10.1021/jo501292q. Epub 2014 Jul 15.

Diastereoselective construction of tetrahydropyridine fused bicyclic structures via three-component domino reaction.

The Journal of organic chemistry

Jie-Ping Wan, Yunfang Lin, Qing Huang, Yunyun Liu

Affiliations

  1. College of Chemistry and Chemical Engineering, Jiangxi Normal University , Nanchang 330022, PR China.

PMID: 25003698 DOI: 10.1021/jo501292q

Abstract

The three-component reactions of enals, electron-deficient alkynes, and hydroxyl-functionalized primary amines for the highly diastereoselective construction of dihydro-3H-benzo[4,5]oxazolo[3,2-a]pyridines, hexahydropyrido[2,1-b][1,3]oxazines, and tetrahydro-2H-oxazolo[3,2-a]pyridines have been achieved. Domino formation of one C-C, two C-N, and one C-O bonds are furnished in these reactions. This bis-annulation protocol allows for the synthesis of fused heterocyclic products of high structural diversity with variation not only of appended fragments but also the ring size of the central backbone.

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