Photolysis of the N-chloroacetyl imide derivative 3-chloroacetyl-7,8-dimethoxy-4,5-dihydro-1H-3- benzazepin-2(3H)-one (2) in aqueous acetonitrile gave 11a-hydroxy-8,9-dimethoxy-5,6,11,11a-tetrahydrooxazolo[2,3-b]benzazepin-3(2H)-one (4) in 81% yield. This representative of a new heterocyclic system could be converted into the 11a-ethoxy derivative (5) by recrystallization from ethanol. The structure of (5) was confirmed by a room-temperature single-crystal X-ray study. Crystals are monoclinic, Cc, a 17.623(9), b 7.550(4), c 12.872(3) Angstrom, beta 112.55(4)degrees, Z = 4; conventional R on \F\ was 0.034 for 1072 'observed' (I > 3 sigma(I)) reflections.
|Journal||Australian Journal of Chemistry: an international journal for chemical science|
|Publication status||Published - 1997|
Bremner, J. B., Rezaie, R., Skelton, B., & White, A. (1997). Synthesis of the Tetrahydrooxazolo[2,3-b]benzazepin-3(2H)-one System and X-Ray Crystal Structure of an 11a-Ethoxy Derivative. Australian Journal of Chemistry: an international journal for chemical science, 50, 759-762. https://doi.org/10.1071/C97009