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Paper | Regular issue | Vol 29, No. 9, 1989, pp.1721-1728
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5024
Synthesis of a 3-Acetoxy-6-phenylpyrone and Its Conversion to a Pyrido[1,4]benzodiazepine

David J. Wustrow and Wendell Wierenga*

*The Upjohn Company, Kalamazoo, MI 49001a, U.S.A.


3-Acetoxy-6-(2-nitro-3,4,5-trimethoxyphenyl)-4-pyrone (5) was prepared via condensation of 3-acetoxy-4-methoxy-3-buten-2-one (2) with the appropriate benzoyl chloride and acid catalyzed cyclization. The intermediate pyrone was converted to the target, 6-oxo-2,5,9,10,11-pentamethoxy-1,2,3,6-tetrahydropyrido[1,6-d][1,4]benzodiazepine (1).