1,3-oxazinan-2-ones from amines and 1,3-diols through dialkyl carbonate chemistry

Rob McElroy, Fabio Aricò, Pietro Tundo*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A one-pot green synthesis of 1,3-oxazinan-2-ones from amines and 1,3-diols in the presence of a dialkyl carbonate and potassium tert-butoxide is described. Four dialkyl carbonates were utilised: dimethyl carbonate, diethyl carbonate, diprop-2-yl carbonate, and tert-butyl methyl carbonate. The more hindered the dialkyl carbonate used, the higher the yield of 1,3-oxazinan-2-one. Four 1,3-diols were reacted having primary-primary, primary-secondary, primary-tertiary, and secondary-tertiary functionalities, with the yield of oxazinanone decreasing with increasing hindrance of the diol. In the case of the diols containing primary and either secondary or tertiary functionality, the substituent(s) were selectively found in the 6-position of the so-formed oxazinanone. The optimized conditions were then employed with different nucleophiles, namely phenylhydrazine, aniline, and n-octylamine.

Original languageEnglish
Pages (from-to)1809-1815
Number of pages7
JournalSynlett
Volume23
Issue number12
Early online date29 Jun 2012
DOIs
Publication statusPublished - Jul 2012

Keywords

  • Cyclisation
  • Dialkyl carbonates
  • Diols
  • Green chemistry
  • Heterocycles

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