Synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives catalysed by sodium dodecyl sulfate (SDS) in neat water

Abstract

A simple and efficient one-pot synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives using catalytic amounts of SDS in water medium is reported. The catalyst can be recovered by simple filtration and reused.

An Efficient Method for the One-pot, Three-Component Synthesis of 3,4-Dihydropyrano[c]chromenes Catalyzed by Nano Al2O3

“…3,4-Dihydropyrano[c] chromene derivatives are generally synthesized via one-pot reaction of an aryl aldehydes, malononitrile and 4-hydroxycoumarin in the presence of several catalysts such as sodium dodecyl sulfate (SDS) 14 , DBU 15 , morpholine 16 , piperidine 17 , K 2 CO 3 under microwave irradiation 18 , sulfonic acid functionalized silica (SiO 2 PrSO 3 H) 19 , trisodium citrate 20 , silica gel 21 , inorganic-organic hybrid magnetic nanocatalyst 22 28 and heteropoly acids 29 . However, in spite of their potential utility, some difficulties still exist, such as expensive or toxic reagent.…”

A Rapid, Efficient and Green Method for Synthesis of 3,3'-Arylmethylene-bis-4-hydroxycoumarins without Use of any Solvent, Catalyst or Solid Surface

“…It is the hemorrhagic agent responsible for the sweet clover disease of cattle and has also been employed for the prevention and treatment of thrombosis 12 . 3,3'-Arylmethylene-bis-4-hydroxycoumarins (3) are usually synthesized by condensing 4-hydroxycoumarin (1) with various aldehydes (aromatic, heterocyclic and α,β-unsaturated) (2) using different catalysts and media [8][9][10][13][14][15][16][17][18][19] . Some of these methods require long reaction time, use of expensive catalysts and organic solvents and tedious work up 8,10 .…”

“…Some of these methods require long reaction time, use of expensive catalysts and organic solvents and tedious work up 8,10 . The current literature shows that there has been a growing trend towards green synthesis of these compounds [13][14][15][16][17][18][19] . However, in such reported green methods use of catalysts, solid surfaces, solvents etc.…”

A Convenient, Eco-friendly, and Efficient Method for Synthesis of 3,3'-Arylmethylene-bis-4-hydroxycoumarins "On-water"

“…16 3,3'-Arylmethylene-bis-4-hydroxycoumarins (3), commonly known as biscoumarins, are usually synthesized by condensing 4-hydroxycoumarin (1) with various aldehydes (aromatic, heterocyclic, and α,β-unsaturated) 2 using different catalysts and media. [13][14][15][17][18][19][20][21][22][23][24] Some of these methods require long reaction time, use of expensive catalysts and organic solvents and tedious work up. 13,15,24 In four recent papers, the said condensation has been reported to be performed in water by employing molecular iodine, 17 ruthenium(III) chloride hydrate 24 or surfactants like TBAB 18 or DDS 19 as catalyst.…”

“…[13][14][15][17][18][19][20][21][22][23][24] Some of these methods require long reaction time, use of expensive catalysts and organic solvents and tedious work up. 13,15,24 In four recent papers, the said condensation has been reported to be performed in water by employing molecular iodine, 17 ruthenium(III) chloride hydrate 24 or surfactants like TBAB 18 or DDS 19 as catalyst. In two other papers, microwave irradiation, either in ethanolic solution or over solid silica surface 20 or in aqueous medium using sulfamic acid as catalyst, 21 has been reported to achieve this goal.…”