Synthesis of 3,5-Isoxazolidinediones and 1H-2,3-Benzoxazine-1,4(3H)-diones from Aliphatic Oximes and Dicarboxylic Acid Chlorides
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- 作者：Robert A. Izydore ; Joseph T. Jones ; Benjamin Mogesa ; Ira N. Swain ; Ronda G. Davis-Ward ; Dwayne L. Daniels ; Felicia Frazier Kpakima ; Sharnelle T. Spaulding-Phifer ; II
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：April 4, 2014
- 年：2014
- 卷：79
- 期：7
- 页码：2874-2882
- 全文大小：390K
- 年卷期：v.79,no.7(April 4, 2014)
- ISSN：1520-6904
文摘
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鈥?b>f) and 2,2鈥?ethylidene-bis[4,4-dialkyl-3,5-isoxazolidinedione]s (9a鈥?b>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鈥?b>e). Products 16 spontaneously decomposed to give N-unsubstituted 1H-2,3-benzoxazine-1,4(3H)-diones (17a鈥?b>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.