Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives

Peng-Hua Li; Jin-Ming Yang; Yin Wei; Min Shi

doi:10.1002/open.201600123

Silver(I)-Catalyzed Intramolecular Cyclizations of Epoxide-Propargylic Esters to 1,4-Oxazine Derivatives

ChemistryOpen. 2016 Dec 13;6(1):21-24. doi: 10.1002/open.201600123. eCollection 2017 Feb.

Authors

Peng-Hua Li¹, Jin-Ming Yang¹, Yin Wei², Min Shi³

Affiliations

¹ Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecule Engineering East China University of Science and Technology 130 Mei Long Road Shanghai 200237 P. R. China.
² State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Linglin Lu Shanghai 200032 P. R. China.
³ Key Laboratory for Advanced Materials and Institute of Fine Chemicals School of Chemistry and Molecule Engineering East China University of Science and Technology 130 Mei Long Road Shanghai 200237 P. R. China; State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Linglin Lu Shanghai 200032 P. R. China.

Abstract

An interesting silver(I)-catalyzed, one-pot intramolecular cyclization of epoxide-propargylic esters is described. A variety of 1,4-oxazine derivatives were obtained through a novel domino sequence, including three-membered ring-opening, 3,3-sigmatropic rearrangement, 6-exo-cycloisomerization and subsequent intramolecular elimination in moderate yields under mild conditions.

Keywords: cyclization; epoxides; propargylic ester; silver catalysis; tandem reaction.