99855-05-7Relevant academic research and scientific papers
1,3-oxazinan-2-ones from amines and 1,3-diols through dialkyl carbonate chemistry
McElroy, Conrobert,Aricò, Fabio,Tundo, Pietro
experimental part, p. 1809 - 1815 (2012/08/29)
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.
The Cycloaddition of Heterocumulenes to Oxetanes in the Presence of Catalytic Amounts of Tetraphenylstibonium Iodide
Fujiwara, Masahiro,Baba, Akio,Matsuda, Haruo
, p. 1659 - 1663 (2007/10/02)
The cycloadditions of carbon dioxide, isocyanates and carbodiimides to oxetanes proceeded in the presence of catalytic amounts of tetraphenylstibonium iodide (1) under mild conditions, affording the corresponding six-membered heterocycles; 1,3-dioxan-2-ones, 1,3-oxazin-2-ones and 1,3-oxazin-2-imines in good yields, respectively.Moreover, the cycloaddition of 2-phenyloxetane proceeded via predominant ring-cleavage at substituted site.
Cycloaddition of Oxetanes with Heterocumulenes Catalyzed by Organotin-Lewis Base Complex
Shibata, Ikuya,Imoto, Takafumi,Baba, Akio,Matsuda, Haruo
, p. 361 - 363 (2007/10/02)
A series of 2-oxazinones 1-8 were synthesized from the cycloaddition reactions of oxetanes with isocyanates by utilizing the complex of diphenyltin diiodide with hexamethylphosphoric triamide (HMPA) as a catalyst.Moreover, the reactions with carbodiimides
