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.
|Number of pages||4|
|Publication status||Published - 31 Dec 1994|