TY - JOUR AU - McElroy, Con Robert; Aricò, Fabio; Tundo, Pietro TI - 1,3-Oxazinan-2-ones from Amines and 1,3-Diols through Dialkyl Carbonate Chemistry SN - 0936-5214 SN - 1437-2096 PY - 2012 JO - Synlett JF - Synlett LA - EN VL - 23 IS - 12 SP - 1809 EP - 1815 ET - 2012/06/29 DA - 2012/07/12 KW - green chemistry KW - cyclisation KW - heterocycles KW - diols KW - dialkyl carbonates AB - 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. PB - © Georg Thieme Verlag DO - 10.1055/s-0031-1290368 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0031-1290368 ER -