ETHYNYLXANTHINES, PREPARATION AND USE AS CALCIUM ION CHANNEL MODULATORS
The present invention relates to novel pharmaceutical compounds, which exhibit ability to act as calcium ion channel modulators, methods for their synthesis and the treatment and/or prevention of various diseases and disorders including deregulated calcium ion channel activity.
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(2016/10/27)
Michael adducts in regioselective synthesis of N-substituted azoles
Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.
Horvath
p. 1183 - 1189
(2007/10/02)
Generation and Properties of N7-Xanthinium Ylides: Reactions of N7-Xanthinium Ylides with Diphenylcyclopropenone and Acetylenic Compounds
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
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Imai, Eiji,Matsumoto, Yukiharu,et al.