K2CO3-Mediated Cyclization and Rearrangement of γ,δ-Alkynyl Oximes To Form Pyridols

Org Lett. 2017 Apr 7;19(7):1574-1577. doi: 10.1021/acs.orglett.7b00389. Epub 2017 Mar 14.

Abstract

A novel K2CO3-mediated cyclization and rearrangement of γ,δ-alkynyl oximes for the synthesis of pyridols is described. The process accomplishes an efficient [1,3] rearrangement of the O-vinyl oxime intermediate which is in situ generated from the intramolecular nucleophilic addition of γ,δ-alkynyl oximes. The reaction employs readily accessible starting materials, tolerates a wide range of functional groups, and gives a variety of synthetically challenging pyridols in good yields.

Publication types

  • Research Support, Non-U.S. Gov't