84: 105513g Further investigations of the interaction of trimethylsilyl azide with substituted maleic anhydrides. Synthesis of 4- and 5-aryl substituted 1,3-(3H)-oxazine-2,6-diones. MacMillan, John H.; Washburne, Stephen S. (Dep. Chem Temple Univ., Philadelphia Pa.). J. Heterocyclic Chem. 1975, 12(6), 1215-20 (Eng).

The reactions of maleic anhydrides 1 (R = H. o-Cl, p-Cl, 3,4-Cl2, p-F. p-MeO) with Me3SiN3 gave mixts. of isomeric 4- and 5-aryl-2H-1,3-(3H)- oxazine-2,6-diones 11 and 111 after hydrolysis with 11 predominating. The yield of 111 is greatest from 1 (R =o-Cl) and substantial for other arylmaleic anhydrides, indicating increased importance of steric effects in these reactions. Chem. Abstr. Vol. 84 105513g.

Return to publications

Return to resume

Return to home page