Cross-aldol reaction of 3-acetyl-2H-chromen-2-one by using Amberlyst 26A as catalyst

ABSTRACT Synthesis of a series of 3-acetylcoumarin-derived chalcones (1a–16a) was catalyzed with Amberlyst 26A in ethanol. Using reusable Amberlyst 26A and biobased solvent ethanol make this method highly ecofriendly and simple. Amberlyst 26A was found to be a highly effective catalyst for cross aldol reaction. The results shown that the method is operationally simple to implement with a wide scope of substrates. GRAPHICAL ABSTRACT

[1]  S. Gholap,et al.  SYNTHESIS AND IN-VITRO ANTIMICROBIAL SCREENING OF 3-CINNAMOYL COUMARIN AND 3- [3- (1H-INDOL-2-YL) -3-ARYL-PROPANOYL]-2H-CHROMEN-2-ONES SOMNATH , 2013 .

[2]  M. Frikha,et al.  Amberlyst-15 and Amberlite-200C: efficient catalysts for aldol and cross-aldol condensation under ultrasound irradiation. , 2013, Ultrasonics sonochemistry.

[3]  S. Gholap,et al.  Synthesis and in-vitro antimicrobial screening of 3-cinnamoyl coumarin and 3-[3-(1H-indol-2-yl)-3-aryl-propanoyl]-2H-chromen-2-ones , 2013 .

[4]  M. Frikha,et al.  Solvent free synthesis of 1,3-diaryl-2-propenones catalyzed by commercial acid-clays under ultrasound irradiation. , 2010, Ultrasonics sonochemistry.

[5]  Hoyun Lee,et al.  Hybrid pharmacophore design and synthesis of isatin-benzothiazole analogs for their anti-breast cancer activity. , 2009, Bioorganic & medicinal chemistry.

[6]  D. V. Kumar,et al.  Synthesis of some coumarinyl chalcones of pharmacological interest. , 2009 .

[7]  G. Peters,et al.  Design of new drug molecules to be used in reversing multidrug resistance in cancer cells. , 2009, Current cancer drug targets.

[8]  O. Petrov,et al.  SOCl2/EtOH: Catalytic system for synthesis of chalcones , 2008 .

[9]  G. Kirsch,et al.  Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin. , 2008, Bioorganic & medicinal chemistry letters.

[10]  Atul Kumar,et al.  Zirconium chloride catalyzed efficient synthesis of 1,3-diaryl-2-propenones in solvent free conditions via aldol condensation ☆ , 2007 .

[11]  T. Narender,et al.  A Simple and Highly Efficient Method for the Synthesis of Chalcones by Using Borontrifluoride‐etherate. , 2007 .

[12]  Ying Zhao,et al.  An Efficient and Practical Procedure for Synthesis of α,α′‐Bis(substituted benzylidene)cycloalkanones Catalyzed by Solid Base SiO2‐OK. , 2006 .

[13]  K. Yeung,et al.  Sonocatalysis in solvent free conditions: An efficient eco-friendly methodology to prepare chalcones using a new type of amino grafted zeolites , 2006 .

[14]  T. Kensler,et al.  The role of Keap1 in cellular protective responses. , 2005, Chemical research in toxicology.

[15]  D. Hadjipavlou-Litina,et al.  Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. , 2004, Current pharmaceutical design.

[16]  M. Zolfigol,et al.  Silica sulfuric acid as an efficient and reusable reagent for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free conditions , 2004 .

[17]  Y. Hayakawa [Structure-activity relationship analysis]. , 2004, Gan to kagaku ryoho. Cancer & chemotherapy.

[18]  Poolsak Sahakitpichan,et al.  A Highly Efficient Synthesis of Lamellarins K and L by the Michael Addition/Ring-Closure Reaction of Benzyldihydroisoquinoline Derivatives with Ethoxycarbonyl-β-nitrostyrenes† , 2004 .

[19]  M. Payá,et al.  Synthesis and inhibitory activity of dimethylamino-chalcone derivatives on the induction of nitric oxide synthase. , 2002, European journal of medicinal chemistry.

[20]  P. Wilairat,et al.  Antimalarial Alkoxylated and Hydroxylated Chalones: Structure−Activity Relationship Analysis , 2001 .

[21]  P. Wilairat,et al.  Antimalarial alkoxylated and hydroxylated chalcones [corrected]: structure-activity relationship analysis. , 2001, Journal of medicinal chemistry.

[22]  E. Ohman,et al.  Heparin and low-molecular-weight heparin: mechanisms of action, pharmacokinetics, dosing, monitoring, efficacy, and safety. , 2001, Chest.

[23]  J. Dimmock,et al.  Bioactivities of chalcones. , 1999, Current medicinal chemistry.

[24]  W. Filippelli,et al.  Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies. , 1998, Farmaco.

[25]  J R Hoult,et al.  Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. , 1996, General pharmacology.

[26]  A. Schönberg,et al.  FUROCHROMONES AND COUMARINS. XI. THE MOLLUSCICIDAL ACTIVITY OF BERGAPTEN, ISOPIMPINILLIN AND XANTHOTOXIN , 1954 .