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Communication | Regular issue | Vol 24, No. 1, 1986, pp.9-12
Published online, 1st January, 1970
DOI: 10.3987/R-1986-01-0009
Reaction of 2,3,6-Trimethylpyrimidin-4-one and Dimethyl Acetylenedicarboxylate

Takao Yamazaki,* Junko Tanii, Yoshiro Hirai, and Katsuhide Matoba

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


Treatment of 2,3,6-trimethylpyrimidin-4-one with dimethyl acetylenedicarboxylate(DMAD) gave tetramethyl 2,5-dimethyl-4-oxo-1,5-diazabicyclo[4.4.1]undecane-2,7,9-triene-7,8,9,10-tetracarboxylate(II) and tetramethyl 1,4,10-trimethyl-2-oxo-1,5-diazacyclodecane-3,5,7,9-tetraene-6,7,8,9-tetracarboxylate (III) in 36.2 and 27.9% yields, respectively. The reduction products with sodium borohydride and the catalytic-reduction products of II or III are also discussed.