1,2-Oxazolines by Addition of Trimethylbenzonitril Oxide to 2-Hydroxyethylamino-1,4-quinones and Their Quinol Derivatives

Article abstract of DOI:10.1007/BF00810865

Addition of trimethylbenzonitril oxide to 2-hydroxyethylamino-1,4-quinones and 3,4-dihydro-4-alkyl-8a-methoxy-2H-1,4-benzoxazin-6(8aH)-ones leads to 7,8,9a,9b-tetrahydro-3aH-1,2-oxazolo<4,5-h>-1,4-benzoxazin-4(6H)-ones.In order to determine constitution and conformation of the addition products an NMR-spectroscopic analysis and an X-ray crystal structure analysis of 6-benzyl-9a-hydroxy-3-mesityl-7,8,9a,9b-tetrahydro-3aH-1,2-oxazolo<4,5-h>-1,4-benzoxazin-4-(6H)-one 3a were carried out at room temperature: C25H26N2O4, M_r = 418.49, monoclinic, P2₁/n, a = 13.716(6), b = 19.993(6), c = 15.348(6) Angstroem, β = 98.55(4) deg, V = 4162(1) Angstroem³, Z = 8, d_x = 1.336 g/cm³, R = 6.77percent, R_w = 4.55percent (2994 observables, 560 parameters).