78440-45-6Relevant academic research and scientific papers
A novel asymmetric synthesis of 2-azetidinones from achiral precursors
Zhou, Feng,Detty, Michael R.,Lachicotte, Rene J.
, p. 585 - 588 (1999)
Asymmetric synthesis of (3S,4S)-3-phenylsulfonyl-4-phenylazetidin-2- ones in up to 46% ee from achiral amines and 2-phenylsulfonyl-3- phenylpropenoyl chloride was achieved with chiral Lewis-acid catalysis by salen-copper(II) complexes derived from (1R,2R)
An ecofriendly approach to the synthesis of 2-imino- and 2-oxo-3-phenylsulfonyl-2H-chromenes
Dias, Tatiana A.,Proen?a, M. Fernanda
, p. 5235 - 5237 (2012/11/07)
An efficient synthesis for 2-imino-3-phenylsulfonyl-2H-chromenes was developed from the Knoevenagel condensation of (phenylsulfonyl)acetonitrile and salicylaldehydes in aqueous sodium carbonate solution, at room temperature. Hydrolysis in aqueous HCl, at
Synthesis and antimicrobial screening of some 3-(phenylsulfonyl)- 2H-chromen-2-ones
Edayadulla,Babu,Ramesh
, p. 1 - 4 (2013/12/04)
In this study, we have investigated the synthetic routes for the preparation of 3-sulfonyl coumarin 3 starting from phenylsulfonyl acetate 2 in the presence of mild base pyridine and piperidine and simple peroxide oxidation of sulphide 6 to sulfones 7 and their antimicrobial activities.
Three-component coupling using arynes and DMF: Straightforward access to coumarins via ortho-quinone methides
Yoshida, Hiroto,Ito, Yu,Ohshita, Joji
supporting information; experimental part, p. 8512 - 8514 (2011/09/16)
ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner. The Royal Society of Chemistry 2011.
Knoevenagel reaction in [MMIm][MSO4]: Synthesis of coumarins
Verdia, Pedro,Santamarta, Francisco,Tojo, Emilia
experimental part, p. 4379 - 4388 (2011/08/06)
The ionic liquid 1,3-dimethylimidazolium methyl sulfate, [MMIm][MSO 4], together with a small amount of water (the amount taken up by the ionic liquid upon exposure to air), acts efficiently as both solvent and catalyst of the Knoevenagel condensation reactions of malononitrile with 4-substituted benzaldehydes, without the need for any other solvent or promoter, affording yields of 92%-99% within 2-7 min at room temperature. When L-proline is used as an additional promoter to obtain coumarins from o- hydroxybenzaldehydes, the reaction also proceeds in high yields. Work-up is very simple and the ionic liquid can be reused several times. Some of the coumarins obtained are described for the first time.
Stereospecificity of diels-Alder reactions validated using Ab initio calculations: Synthesis of novel coumarin and phenanthridine derivatives
El-Shafei,Fadda,Abdel-Gawad,Youssif
experimental part, p. 2954 - 2972 (2009/12/03)
A new series of coumarin derivatives (2-5) was synthesized by reaction of phenylsulfonylacetonitrile (1) with 2-hydroxy-1-naphthaldehyde and/or salicyaldehyde. Compounds 3 and 5 were converted to the corresponding phenanthridine analogs 6 and 7, respectiv
Samarium (III) triiodide catalysed reaction of salicylaldehydes with active methylene compounds
Chen,Zhang
, p. 394 - 395 (2007/10/03)
The unambiguous synthesis and isolation of 2-oxo-2H-1-benzopyran derivatives are described. The Knoevenagel condensation of 2-hydroxy benzaldehydes with active methylene compounds catalysed by samarium triiodide resulted in coumarium derivatives in fair yields under refluxing conditions.
Simple and efficient one-pot preparation of 3-substituted coumarins in water
Brufola, Gianluca,Fringuelli, Francesco,Piermatti, Oriana,Pizzo, Ferdinando
, p. 1257 - 1266 (2007/10/03)
3-Cyanocoumarin and seven derivatives [4-Me; 6-NO2; 7-OH; 7-OMe; 8-OH; 5,7-OMe; 6,7-(-CH=CH-)-2] and eight coumarins substituted at C-3 (CO2Et; NO2; Ph; p-NO2-C6H4; Ph-SO2; 2-pyridyl; 2-thienyl; 2-benzothiazolyl) were prepared, on multigram scale by a one-pot procedure in water alone, by the Knoevenagel reaction of o-hydroxyaryl aldehydes and o-hydroxyacetophenone with acetonitriles. The yields are high and the procedure does not require organic solvents. The reactions carried out in heterogeneous aqueous phase, sometimes in the presence of a surfactant, always have higher yields than the same reactions executed in homogeneous ethanolic medium.
Synthesis of Sulfonylsubstituted Heterocycles by Cyclocondensation of Sulfones with Bifunctionalised Compounds
Lemcke, Thomas,Messinger, Paul
, p. 1 - 4 (2007/10/02)
2-Sulfonylketendithioacetales (1), alkyl-sulfonylacetates (6), 2-sulfonyl-acetophenones (9) and -nitriles (12) react by cyclocondensation with bifunctionalised compounds 2, 4, 7, 10 and 13 yielding the sulfonylsubstituted chinoline- 3, chinolone- 5, barbituric acid- 8, pyrane- 11 and coumarine 15 derivatives.
Synthesis of 3-Coumaryl Phenyl Sulfones or Sulfoxides
Merchant, J.R.,,Shah, P.J.,
, p. 441 - 442 (2007/10/02)
An unambiguous synthesis of a number of 3-coumaryl phenyl sulfones or sulfoxides have been described which were obtained by the oxidation of the corresponding sulfides with hydrogen peroxide.The sulfides were prepared by the Perkin-Oglialore reaction of o-hydroxyaldehyde with the sodium salt of different S-phenyl thioacetic acids.The sulfones did not exhibit any appreciable antituberculous activity in the preliminary screening tests.
