title: Synthesis of 3,5-isoxazolidinediones and 1H-2,3-benzoxazine-1,4(3H)-diones from aliphatic oximes and dicarboxylic acid chlorides.
abstract: 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.
authors.affiliation: Department of Chemistry, North Carolina Central University , Durham, North Carolina 27707, United States.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Izydore
authors.forename: Joseph T
authors.initials: JT
authors.lastname: Jones
authors.forename: Benjamin
authors.initials: B
authors.lastname: Mogesa
authors.forename: Ira N
authors.initials: IN
authors.lastname: Swain
authors.forename: Ronda G
authors.initials: RG
authors.lastname: Davis-Ward
authors.forename: Dwayne L
authors.initials: DL
authors.lastname: Daniels
authors.forename: Felicia Frazier
authors.initials: FF
authors.lastname: Kpakima
authors.forename: Sharnelle T
authors.initials: ST
authors.lastname: Spaulding-Phifer
mesh_terms: D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D003998:Dicarboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D010091:Oximes / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D048588:Benzoxazines; D002712:Chlorides; D003998:Dicarboxylic Acids; D023303:Oxazolidinones; D010091:Oximes; D011799:Quinazolines