132356-47-9Relevant academic research and scientific papers
The reactivity of 4-hydroxycoumarin under heterogeneous high-intensity sonochemical conditions
Cravotto, Giancarlo,Nano, Gian Mario,Palmisano, Giovanni,Tagliapietra, Silvia
, p. 1286 - 1291 (2007/10/03)
High-intensity ultrasounds have been employed in the synthesis of 4-hydroxycoumarin derivatives, using mainly water as reaction medium. Marked improvements of reaction rates, chemoselectivity and product yields have been observed on comparing sonochemical with ordinary conditions. In the alkylation of a series of allyl and benzyl bromides a pathway switch occured to yield 3-alkyl-4-hydroxycoumarin derivatives.
The Chemistry of Coumarin Derivatives Synthesis of 3-Alkyl-4-hydroxycoumarins by Reductive Fragmentation of 3,3'-Alkylidene-4,4'-dihydroxybis
Appendino, Giovanni,Cravotto, Giancarlo,Tagliapietra, Silvia,Ferraro, Stefano,Nano, Gian Mario,Palmisano, Giovanni
, p. 1451 - 1458 (2007/10/02)
Treatment of 3,3'-alkylidene-4,4'-dihydroxybis 1 with NaBH3CN in refluxing MeOH affords 3-alkyl-4-hydroxycoumarins 2 and 4-hydroxycoumarin (3; Scheme 1).The reaction may 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 --> 2 is suggested by Diels-Alder and nucleophilic trapping of the alkylidenechromandiones C as well as from cross-over experiments with coumarins other than 3 (see Scheme 2).The reductive fragmentation of 1 allows the chemo- and regioselective synthesis of a variety of 3-alkyl-4-hydroxycoumarins 2 (see Table).
