Synthesis of the Tetrahydrooxazolo[2,3-b][3]benzazepin-3(2H)-one System and X-Ray Crystal Structure of an 11a-Ethoxy Derivative

J.B. Bremner, R. Rezaie, Brian Skelton, Allan White

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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][3]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.
Original languageEnglish
Pages (from-to)759-762
JournalAustralian Journal of Chemistry: an international journal for chemical science
Publication statusPublished - 1997


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