Microwave‐Initiated Reactions: Pechmann Coumarin Synthesis, Biginelli Reaction, and Acylation.

Manhas, M. S.; Ganguly, Subhendu N.; Mukherjee, Somdatta; Jain, Amit; Bose, Ajay K.

doi:10.1002/chin.200628030

Cited by 3 publications

(3 citation statements)

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“…Synthesis of 3-styrylcoumarins was performed following the scheme 1, which began with formation of the coumarin (2) by microwave assisted Pechmann reaction between resorcinol (1) and ethyl acetoacetate (Manhas et al, 2006). Compound (3), obtained by microwave assisted Williamson etherification reaction of coumarin (2) (Otero et al, 2014) in 85% yield, was brominated with NBS (Adhikari et al, 2002) to give the alkyloxybromocoumarin (4) in 75% yield.…”

Section: Synthesis Of 3-styrylcoumarinsmentioning

confidence: 99%

Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins

et al. 2018

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A series of styrylcoumarins were obtained via Mizoroki-Heck reactions between 3-bromo-4-methyl-7-(octyloxy)-2H-chromen-2-one or 2-oxo-2H-chromen-7-yl trifluoromethanesulfonate and functionalized styrenes. The structures of the products were elucidated by spectroscopic analysis. All compounds were evaluated against SW480 and CHO-K1 cell lines. A number of hybrids showed good antiproliferative activity. Among the tested compounds, hybrids 6e, 10c and 10d, exhibited the highest activity (IC50-SW480/48h = 6,92; 1,01 and 5,33 µM, respectively) and selectivity (IS48h = >400; 67,8 and 7,2, respectively). In addition, these compounds were able to preserve their activities over time. The results achieved by these hybrids were even better than the lead compounds (coumarin and resveratrol) and the standard drug (5-FU). As regards structure-activity relationship it seems that the location of the styryl group on the coumarin structure and the presence of the hydroxyl group on the phenyl ring were determinant for the activity.

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Section: Synthesis Of 3-styrylcoumarinsmentioning

confidence: 99%

Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins

et al. 2018

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“…The moisture absorbed during the grinding made the reaction mixture homogeneous, and the product could be isolated by dilution with ice-cold water. A microwave-accelerated variant of the reaction in the presence of p-TsOH has been investigated (Entry 3) [ 15 ]. Sulfamic acid [ 16 ] and meglumine sulfate [ 17 ] were found to be efficient and mild acids for the synthesis of 4-arylcoumarins (Entries 4–6).…”

Section: Synthetic Routes Toward Central 2-pyrone Of 4-arylcoumarimentioning

confidence: 99%

Recent Advances in Synthesis of 4-Arylcoumarins

et al. 2018

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4-Arylcoumarins (4-aryl-2H-1-benzopyran-2-one), also known as neoflavones, comprise a minor subclass of naturally occurring flavonoids. Because of their broad-spectrum biological activities, arylcoumarins have been attracting the attention of the organic and medicinal chemistry communities, and are considered as an important privileged scaffold. Since the development of Pechmann condensation, a classical acid-catalyzed condensation between phenol and β-keto-carboxylic acid, several versatile and efficient synthetic approaches for 4-arylcoumarins have been reported. This review summarizes recent advances in the synthesis of the 4-arylcoumarin scaffold by classifying them based on the final bond-formation type. In particular, synthetic methods executed under mild and highly efficient conditions, such as solvent-free reactions and transition metal catalysis, are highlighted.

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“…On the other hand, in recent years, the concept of speeding up the synthetic transformations by microwave activation has created a lot of interest in organic synthesis [ 34 ]. The coupling of microwave heating under solvent-free conditions in chemical processeses catalyzed by solids gives rise to an enhancement of the reaction rate, ease of work-up and high yields [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

et al. 2017

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A suitable methodology of synthesis of coumarin derivatives by Pechmann reaction over heterogeneous solid acid catalysts in a free solvent media under microwave irradiation is described. Resorcinol, phenol and ethyl acetoacetate were selected as model reactants in the Pechmann condensation. The catalytic activity of several materials—Amberlyst-15, zeolite β and sulfonic acid functionalized hybrid silica—in solvent-free microwave-assisted synthesis of the corresponding coumarin derivatives has been investigated in detail. 7-Hydroxy-4-methylcoumarin and 4-methylcoumarin were obtained in 97% and 43% yields, respectively, over Amberlyst-15. This was the most active catalyst in the Pechmann reaction under studied conditions.

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Microwave‐Initiated Reactions: Pechmann Coumarin Synthesis, Biginelli Reaction, and Acylation.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 3 publications

References 1 publication

Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins

Synthesis and antiproliferative activity of 3- and 7-styrylcoumarins

Recent Advances in Synthesis of 4-Arylcoumarins

Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

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