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Communication | Special issue | Vol 39, No. 2, 1994, pp.509-512
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)80
HIV Reverse Transcriptase Inhibitors: A Concise Ene Reaction Based Synthesis of the 7,8-Dihydro-6H,12H-azepino[2,1-b]quinazoline System, and Its Reaction with Nitrile Oxides

Catharine Goulaouic-Dubois, David R. Adams, Angele Chiaroni, Claude Riche, Frank W. Fowler,* and David S. Grierson*

*Department of Chemistry, State University of New York ar Stony Brook, Stony Brook, New York 11794-3400, U.S.A.

Abstract

The reaction of amide (5), obtained in two steps from 2-amino benzophenone (4) with triflic anhydride, followed by treatment of the in situ generated imodyl triflate (7) with LiCN led to exclusive formation of the tetrahydroquinazoline (10). Thermolysis of this intermediate promoted an ene reaction leading to the azepino-quinazoline (11) (63% yield). The 1,3-dipolar cycloaddition between this product and nitrile oxide (12) proved chemoselective, producing the novel pentacyclic oxadiazine (14) as a 7:3 mixture of diastereomers in 79% yield.