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Communication | Special issue | Vol 54, No. 2, 2001, pp.601-606
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9011
Studies on Pyrimidine-annulated Heterocycles: Synthesis and Function of Novel 9-Substituted Cyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-diones

Tohru Takayasu, Yutaka Mizuta, and Makoto Nitta*

*Department of Chemistry, School of Science and Engineering, Materials Research Laboratory for Bioscience and Photonics, Waseda University, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

A new short synthesis of 9-substituted cyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-diones has been accomplished by the reaction of 3-methyl-, 3-butyl-, and 3-phenylbarbituric acids with 2-chlorotropone in an enolate-substitution process and subsequent dehydrative cyclization by using CF3CO2H. These novel compounds exhibited a strong function in oxidizing some alcohols under neutral and aerobic conditions to give an aldehyde or ketones in anÅ@autorecycling process, while they are hydrogenated to mixtures of 5,7-, 1,7-, andÅ@3,7-dihydrocyclohepta[b]pyrimido[5,4-d]furan-8,10(9H)-dione derivatives.