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Paper | Regular issue | Vol 63, No. 2, 2004, pp.319-331
Published online, 8th December, 2003
DOI: 10.3987/COM-03-9945
Novel Synthesis, Properties, and Structural Characteristics of 1,6-Dialkyl-pyrimido[5,4-e][n](2,4)pyridinophane-5,7-(1H,6H)-diones

Makoto Nitta,* Hiromi Kanda, Hiroyuki Yamamoto, and Shin-ichi Naya

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

Abstract

Novel synthesis of the 1,6-dialkylpyrimido[5,4-e][n](2,4)pyridinophane-5,7(1H,6H)-diones (n = 11, 9, 6) (5,7-polymethylene-substituted 8-alkylpyrido[2,3-d]pyrimidine-2,4(3H,8H)-diones) consists of allowing 3-methyl-6-benzylaminouracil to react with cycloalk-2-enones. Their chemical and electrochemical properties as well as structural characteristics are studied on the basis of their spectroscopic properties, cyclic voltammetry, X-Ray analysis, and theoretical calculations. Deformation of the pyridine ring of a [6](2,4)pyridinophane derivative is observed by X-Ray analysis. Furthermore, isolation of a dihydrogenated [5](2,4)pyridinophane derivative and its unsuccessful dehydrogenation reaction leading to the first example of a [5](2,4)pyridinophane derivative are investigated as well.