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…

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

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Citation Number: 40

Abstract

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 ...

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