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

McElroy, Con, AricÃ, F. and Tundo, P. (2010) 1,3-oxazinan-2-ones from amines and 1,3-diols through dialkyl carbonate chemistry. Accounts and Rapid Communications in Chemical Synthesis (SYNLETT), 23 (12). pp. 1809-1815. ISSN 0936-5214

Full content URL: https://doi.org/10.1055/s-0031-1290368

Full text not available from this repository.

Item Type:Article
Item Status:Live Archive


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. © 2012 Georg Thieme Verlag Stuttgart . New York.

Keywords:1,3 diol derivative, unclassified drug, article, controlled study, cyclization, one pot synthesis
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
Related URLs:
ID Code:54771
Deposited On:15 May 2023 13:44

Repository Staff Only: item control page