Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines

Zhong-Jian Cai; Chao Yang; Shun-Yi Wang; Shun-Jun Ji

doi:10.1039/c5cc06510k

Palladium-catalyzed highly regioselective 6-exo-dig cyclization and alkenylation of ortho-ethynylanilides: the synthesis of polyene-substituted benzo[d][1,3]oxazines

Chem Commun (Camb). 2015 Sep 28;51(75):14267-70. doi: 10.1039/c5cc06510k. Epub 2015 Aug 26.

Authors

Zhong-Jian Cai¹, Chao Yang, Shun-Yi Wang, Shun-Jun Ji

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, People's Republic of China. [email protected] [email protected].

PMID: 26308364
DOI: 10.1039/c5cc06510k

Abstract

A Pd-catalyzed highly regioselective 6-exo-dig cyclization/alkenylation reaction of ortho-ethynylanilides has been developed. This tandem cross-coupling protocol represents a simple, efficient, step- and atom-economic approach for the construction of scarcely known polyene-substituted benzo[d][1,3]oxazines in moderate to excellent yields with a broad substrate scope.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Anilides / chemistry*
Benzoxazines / chemical synthesis*
Benzoxazines / chemistry
Catalysis
Cyclization
Molecular Structure
Organometallic Compounds / chemistry*
Palladium / chemistry*
Polyenes / chemistry*
Stereoisomerism

Substances

Anilides
Benzoxazines
Organometallic Compounds
Polyenes
Palladium