A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU

Hwang, In Taek; Lee, Sun‐Ah; Hwang, Jung Yeon; Lee, Kee‐In

doi:10.3390/molecules16086313

Cited by 27 publications

(61 citation statements)

References 30 publications

(33 reference statements)

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“…4-Arylcoumarins 59 have been synthesized in good yields employing Kostanecki reaction between 2-hydroxybenzophenones 57 and acetic anhydride 58 in the presence of DBU under mild condition (Figure 17) [107].…”

Section: Kostanecki Reactionmentioning

confidence: 99%

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One-Pot Synthesis of Coumarin Derivatives

Ansary¹,

Taher²

2020

Phytochemicals in Human Health

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Coumarin derivatives have a myriad of applications in medical science, biomedical research, and many industrial branches. For this reason, many efforts are being dedicated to the development of novel and more practical methods for synthesizing these compounds. This chapter describes several methods of one-pot synthesis of coumarin derivatives, including von Pechmann condensation, Knoevenagel condensation, Baylis-Hillman reaction, Michael addition, Kostanecki reaction, vinyl phosphonium salt-mediated electrophilic reaction, and Heck-lactonization reaction. The methods are compared with each other, and the advantages and disadvantages of each of them are addressed.

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Section: Kostanecki Reactionmentioning

confidence: 99%

“…The mechanism of the Kostanecki reaction is outlined in Figure 18. Similarly, 3,4-disubstituted coumarins 65 are isolated from readily available 2-acyloxybenzophenones 64 under Kostanecki reaction conditions (Figure 19) [107].…”

Section: Kostanecki Reactionmentioning

confidence: 99%

One-Pot Synthesis of Coumarin Derivatives

Ansary¹,

Taher²

2020

Phytochemicals in Human Health

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“…The Kostanecki-Robinson reaction has been used for coumarin [ 84 , 85 ] or chromone [ 86 ] synthesis by O -acylation of 2-hydroxyarylketones with an aliphatic anhydride, followed by aldol condensation. In 2011, Lee et al published a synthesis method for 4-arylcoumarins 62 based on the DBU-mediated Kostanecki reaction [ 87 ] ( Scheme 11 A). A previous approach to 4-arylcoumarins by the Kostanecki-Robinson reaction had several drawbacks, including harsh reaction conditions and low yields.…”

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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“…The structure makes the molecule highly reactive and causes it to undergo various transformations [1][2][3][4]. Several novel organic transformations with alkynes have been explored to build valuable molecular skeletons in recent years [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Among these, difunctionalization of alkynes is an efficient and straightforward strategy for the synthesis of functionalized compounds, which can be transformed into diverse organic skeletons.…”

Section: Introductionmentioning

confidence: 99%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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Visible light promoted difunctionalization of alkynes is reviewed. The difunctionalization reaction is achieved by different reagents. Radicals such as carbon (sp 3), carbon (sp 2), and other heteroatom (P, S, N, Se, O, and halide) radicals initiated by visible light can undergo radical addition to a carbon-carbon triple bond. Upon further transformation, the desired difunctionalized products are obtained. Some organometallic complexes can be activated by visible light; the difunctionalization of alkynes is catalyzed by these species. Other reagents like 1,3-dipole precursors could also react with alkynes to give difunctionalization products; here, the 1,3-dipole derivatives are obtained by visible light photocatalysis. So far, the strategy has been succeeded in the formation of CC bonds and C-X bonds. Several valuable chemical skeletons have been constructed under mild conditions. However, high regio-and stereoselectivities in some direct difunctionalization methodologies are yet to be achieved.

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A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU

Cited by 27 publications

References 30 publications

One-Pot Synthesis of Coumarin Derivatives

One-Pot Synthesis of Coumarin Derivatives

Recent Advances in Synthesis of 4-Arylcoumarins

Visible light promoted difunctionalization reactions of alkynes

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