Synthesis 2017; 49(09): 1955-1968
DOI: 10.1055/s-0036-1588748
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© Georg Thieme Verlag Stuttgart · New York

Metal-Free Synthesis of Oxazinones and Their Reductive Ring Opening to Provide Cyclopropyl Carbinols

Alexander J. Craig
Department of Chemistry, University of Otago, Dunedin, New Zealand   Email: bhawkins@chemistry.otago.ac.nz
,
Bill C. Hawkins*
Department of Chemistry, University of Otago, Dunedin, New Zealand   Email: bhawkins@chemistry.otago.ac.nz
› Author Affiliations
Further Information

Publication History

Received: 03 February 2017

Accepted after revision: 23 February 2017

Publication Date:
14 March 2017 (online)


Abstract

General routes for the synthesis of 1,3-oxazin-4-ones are discussed, with particular attention paid to recent developments in the field. The syntheses of amine functionalised cyclopropyl carbinols via a hydride-mediated reduction of various 5-chloroethyl-1,3-oxazin-4-enones in moderate to good yield are disclosed. This new method provides an opportunity to access greater structural diversity within these useful synthetic building blocks.

Supporting Information