30237-79-7Relevant academic research and scientific papers
Generation and Properties of N7-Xanthinium Ylides: Reactions of N7-Xanthinium Ylides with Diphenylcyclopropenone and Acetylenic Compounds
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Imai, Eiji,Matsumoto, Yukiharu,et al.
, p. 1328 - 1332 (2007/10/02)
Xanthinium N7-ylides were generated in situ from 7-substituted 9-methylxanthinium tosylates (2) using n-BuLi in tetrahydrofuran or Et3N in MeCN.The xanthinium N7-ylides (3) generated using Et3N 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.N7-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.Keywords - xantinium N7-ylide; cycloaddition; dimethyl acetylenedicarboxylate; methyl propiolate; diphenylcyclopropenone; 5-pyrrol-1-yluracil; pyrrolopteridine; isocaffeine
