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Paper | Regular issue | Vol 57, No. 3, 2002, pp.491-499
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9425
On the Reactions of 6-Phosphoranylideneaminouracils and Related 6-Aminouracils with 2,4,6-Cyclooctatrienone: Reactions of the Intermediates of Uracil-annulated 8-Azabicyclo[5,3,1]undecatetraene Ring Systems

Makoto Nitta* and Hiromi Kanda

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

The reaction of 1,3-dimethyl-6-phosphoranylideneaminouracil (4) with 2,4,6-cyclooctatrienone (7) in AcOH gives an intermediacy of uracil-annulated 8- azabicyclo[5.3.1]undeca-2,4,7,9-tetraene (9), which results in the formation of 9- acetoxy-5a,10-methano-2,4-dimethyl-2H-5,5a,6,8a,9,10-hexahydrocyclopent[b]-pyrimido[5,4-f]azepine-1,3(4H)-dione and 1,3,7- and 1,3,5-trimethylpyrido[2,3-d]pyrimidine-2(1H),4(3H)-diones (12 and 13) after several reaction sequences. A similar reaction using 6-amino-1,3-dimethyluracil (5) also afforded the same products probably via uracil-annulated 8-azabicyclo[5.3.1]undeca-2,4,6,9-tetraene (14). A similar intermediate is also postulated in the reaction of 3-methyl-6- methylaminouracil (6) with 2,4,6-cyclooctatrienone, and results in the formation of 9-acetoxy-5a,10-methano-2,4,5-trimethyl-2H-5,5a,6,8a,9,10-hexahydrocyclopent[b]pyrimido[5,4-f]azepine-1,3(4H)-dione (26), 3,7,8- and 3,5,8-trimethylpyrido[2,3-d]pyrimidine-2(3H),4(8H)-diones (27 and 28).