Generation and Properties of N^7-Xanthinium Ylides : Reactions of N^7-Xanthinium Ylides with Diphenylcyclopropenone and Acetylenic Compounds

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Xanthinium N^7-ylides were generated in situ from 7-substituted 9-methylxanthinium tosylates (2) using n-BuLi in tetrahydrofuran or Et_3N in MeCN. The xanthinium N^7-ylides (3) generated using Et_3N in MeCN reacted with diphenylcyclopropenone to give pyrone derivatives and isocaffeine in good yields. The reactions of 3a-b with dimethyl acetylenedicarboxylate or methyl propiolate (MP) afforded 5-pyrrol-1-yluracils in moderate yields. N^7-Methoxycarbonylmethylide (3c) reacted with MP to give a pyrrolopteridine derivative together with a 5-pyrrol-1-yluracil derivative. Furthermore, the dihydropyrrolopurine derivative (7), a primary 1,3-dipolar cycloaddition product, was detected by nuclear magnetic resonance measurement of the products.
社団法人日本薬学会の論文
1986-03-25