22105-01-7Relevant academic research and scientific papers
Pd/C-catalyzed alkylation of heterocyclic nucleophiles with alcohols through the "borrowing hydrogen" process
Putra, Anggi Eka,Oe, Yohei,Ohta, Tetsuo
, p. 7799 - 7805 (2015/12/31)
The alkylation of heterocyclic compounds is important for the synthesis of various biologically active compounds. In this paper, we present the development of a Pd/C-catalyzed alkylation of heterocyclic compounds using alcohols as the alkylating agents. T
Efficient C-3 reductive alkylation of 4-hydroxycoumarin by dehydrogenative oxidation of benzylic alcohols through ruthenium catalysis
Montagut-Romans,Boulven,Lemaire,Popowycz
, p. 1794 - 1801 (2014/05/06)
A practical route to prepare 4-hydroxycoumarin derivatives functionalized at the C-3 position is described through a catalytic coupling reaction between 4-hydroxycoumarin and a series of substituted benzylic alcohols. The reaction is conducted in the pres
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).
