The chemistry of coumarin derivatives. Part 3. Synthesis of 3??alkyl??4??hydroxycoumarins by reductive fragmentation of 3, 3′??alkyiidene??4, 4′??dihydroxybis [ …

G Appendino, G Cravotto, S Tagliapietra…

文献索引：Appendino, Giovanni; Cravotto, Giancarlo; Tagliapietra, Silvia; Ferraro, Stefano; Nano, Gian Mario; Palmisano, Giovanni Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1451 - 1458

全文：HTML全文

被引用次数: 40

摘要

Abstract Treatment of 3, 3′-alkylidene-4, 4′-dihydroxybis [coumarins] 1 with NaBH 3 CN in refluxing MeOH affords 3-alkyl-4-hydroxycoumarins 2 and 4-hydroxycoumarin (3; Scheme 1). The reaction might take place via hydride trapping of alkylidenechromandiones C formed from 1 in a retro-Michael reaction. Such a retro-Michael reaction of 1 might be biologically relevant. The presence of C during the reductive fragmentation 1 [RIGHTWARDS ARROW ...

~88%

~78%

Model studies for a molecular mechanism of action of oral an...

[Silverman, Richard B. Journal of the American Chemical Society, 1981 , vol. 103, # 13 p. 3910 - 3915]

Synthesis of Coumarins, 4-Hydroxycoumarins, and 4-Hydroxyqui...

[Dittmer, Donald C.; Li, Qun; Avilov, Dimitry V. Journal of Organic Chemistry, 2005 , vol. 70, # 12 p. 4682 - 4686]

Reaction of Phosgeniminium Salts with Enolates Derived from ...

[Morris, Joel; Luke, George P.; Wishka, Donn G. Journal of Organic Chemistry, 1996 , vol. 61, # 9 p. 3218 - 3220]

The Alkylation of Coumarin at C-3 of 4-Hydroxycoumarin

[Tabakovic, Ibro; Tabakovic, Katmerka; Gaon, Igor Organic Preparations and Procedures International, 1997 , vol. 29, # 2 p. 223 - 226]