Synlett 2012; 23(12): 1809-1815
DOI: 10.1055/s-0031-1290368
letter
© Georg Thieme Verlag Stuttgart · New York

1,3-Oxazinan-2-ones from Amines and 1,3-Diols through Dialkyl Carbonate Chemistry

Con Robert McElroy
Università Ca’ Foscari di Venezia, Dipartimento Scienze Ambientali, Informatica e Statistica, Dorsoduro 2137, 30123 Venice, Italy, Fax: +39(041)2348620   Email: tundop@unive.it
,
Fabio Aricò
Università Ca’ Foscari di Venezia, Dipartimento Scienze Ambientali, Informatica e Statistica, Dorsoduro 2137, 30123 Venice, Italy, Fax: +39(041)2348620   Email: tundop@unive.it
,
Pietro Tundo*
Università Ca’ Foscari di Venezia, Dipartimento Scienze Ambientali, Informatica e Statistica, Dorsoduro 2137, 30123 Venice, Italy, Fax: +39(041)2348620   Email: tundop@unive.it
› Author Affiliations
Further Information

Publication History

Received: 16 January 2012

Accepted after revision: 19 April 2012

Publication Date:
29 June 2012 (online)


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.

Supporting Information

 
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