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

Alexander J. Craig; Bill C. Hawkins

doi:10.1055/s-0036-1588748

Synthesis, Table of Contents

Synthesis 2017; 49(09): 1955-1968
DOI: 10.1055/s-0036-1588748

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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

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Abstract

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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.

Key words

heterocycles - ring opening - ring closure - reduction - cyclopropane

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References

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