126293-11-6Relevant academic research and scientific papers
Synthesis of 3,5-isoxazolidinediones and 1 H -2,3-benzoxazine-1,4(3 H)-diones from aliphatic oximes and dicarboxylic acid chlorides
Izydore, Robert A.,Jones, Joseph T.,Mogesa, Benjamin,Swain, Ira N.,Davis-Ward, Ronda G.,Daniels, Dwayne L.,Kpakima, Felicia Frazier,Spaulding-Phifer, Sharnelle T.
, p. 2874 - 2882 (2014)
The synthesis of the title compounds was carried out by reacting dicarboxylic acid chlorides with oximes in the presence of excess triethylamine. Disubstituted malonyl chlorides gave 2-alkenyl-4,4-dialkyl-3,5- isoxazolidinediones (8a-f) and 2,2′-ethylidene-bis[4,4-dialkyl-3,5- isoxazolidinedione]s (9a-f). Compounds 9 were formed from 8 and its N-unsubstituted 3,5-isoxazolidinedione decomposition product. Phthaloyl chlorides reacted with acetone oxime to yield 3-(1-methylethenyl)-1H-2,3- benzoxazine-1,4(3H)-diones (16a-e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a-e) at rates that were dependent on temperature and solvent. Kinetic studies showed that two of the compounds decomposed by zero-order kinetics under neutral conditions. Butanedioyl chloride did not produce a cyclic product.
