One-Pot Synthesis of Coumarin Derivatives

Ansary, Inul; Taher, Abu

doi:10.5772/intechopen.89013

Cited by 12 publications

(12 citation statements)

References 128 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, a phenol-containing electron-withdrawing group (EWG), for example, 4-chlorophenol ( 32 ), failed to undergo the Pechmann condensation reaction, which may be due to low nucleophilicity and/or mild reaction medium under investigation (Table , entry 13). Moreover, as shown in the literature, − the parent phenol does not react at all to deliver the corresponding desired product 35 (Table , entry 14). As expected, our efforts in this direction were also futile (no starting material was consumed), although we have raised the temperature of the reaction mixture to 140 °C and also stirred the reaction for several days.…”

Section: Resultsmentioning

confidence: 55%

An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins

Rather

Ali

2022

ACS Omega

View full text Add to dashboard Cite

Herein, we report a green and efficient synthetic route for the construction of diverse functionalized coumarins in good-to-excellent yields (60–98%) via the Pechmann condensation. The optimized synthetic route involves a biodegradable, reusable, and inexpensive deep eutectic solvent (DES) of choline chloride and l -(+)-tartaric acid in a ratio of 1:2 at 110 °C. Interestingly, phloroglucinol and ethyl acetoacetate, upon reaction, furnished the functionalized coumarin ( 20 ) in 98% yield within 10 min. On the other front, the same DES at relatively lower reaction temperature (90 °C) was found to provide the bis-coumarins in decent yields (81–97%) within 20–45 min. Moreover, this particular method was found to be quite effective for large-scale coumarin synthesis without noteworthy reduction in the yields of the desired products. Noticeably, in this versatile approach, the DES plays a dual role as solvent as well as catalyst, and it was effectively recycled and reused four times with no significant drop-down in the yield of the product.

show abstract

Section: Resultsmentioning

confidence: 55%

An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins

Rather

Ali

2022

ACS Omega

View full text Add to dashboard Cite

show abstract

“…The classic and most frequently used one-step methods for the synthesis of coumarin derivatives include the Perkin reaction, von Pechmann condensation, Knoevenagel condensation, Baylis-Hillman reaction, Michael addition, Kostanecki reaction, and Heck lactonization reaction [31] (Scheme 1). The coumarin synthesis was first described by Perkin in 1868 [32,33].…”

Section: Methods For the Synthesis Of The Coumarin Corementioning

confidence: 99%

Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

Szwaczko

2022

Inorganics

View full text Add to dashboard Cite

For several decades, coumarins have attracted considerable attention due to the fact of their application in diverse fields such as medical science and biomedical research as well as several industrial branches. Recently, many compounds containing the coumarin moiety have been intensively studied, mainly due to the fact of their biological activities such as antitumor, antioxidative, anti-HIV, vasorelaxant, antimicrobial, and anticancer. They are also widely used as fluorescent dyes and probes because of their great structural flexibility and large fluorescent quantum yields. For this reason, numerous attempts have been made to develop new and more practical methods for the synthesis of these compounds. This review aims at providing a comprehensive overview of coumarin synthesis methods by direct C–H bond activation in order to demonstrate the current state-of-the-art methods as well as the current limitations.

show abstract

“…Ultrasonic irradiation also accelerates syntheses and provides the products in good yield [71,76,77]. The properties of many catalysts have been discussed in recently published reviews [78,79].…”

Section: Coumarins: Synthesis Structures and Propertiesmentioning

confidence: 99%

“…Typically used basic catalysts include proline, lysine, DBU, and piperidine. Similar to the Pechmann reaction, microwave or ultrasonic irradiation give better results than the temperature driven process (for details see [79]). 3,4-Substituted coumarins (Scheme 4, 16) can been prepared by other methods involving the formation of a 3-4 carbon-carbon bond [81].…”

Section: Coumarins: Synthesis Structures and Propertiesmentioning

confidence: 99%

Antagonists of Vitamin K—Popular Coumarin Drugs and New Synthetic and Natural Coumarin Derivatives

et al. 2020

View full text Add to dashboard Cite

Many natural coumarins and their chemically synthesized analogs and derivatives exert diverse properties, such as anticancer, antioxidant, anti-inflammatory, or anticoagulant, with the latter being of the utmost importance. The widely used warfarin, acenocoumarol, and phenprocoumon exert anticoagulant properties by inhibiting the vitamin K epoxide reductase complex. In this interdisciplinary review, we present biochemical principles of the coagulation processes and possible methods for their tuning based on the use of coumarins. We also summarize chemical methods of synthesis of coumarins and discuss structures and properties of those that have been used for a long time, as well as newly synthesized compounds. Brief information on the clinical use of coumarins and other anticoagulant drugs is given, including the severe effects of overdosing and methods for reversing their action.

show abstract

One-Pot Synthesis of Coumarin Derivatives

Cited by 12 publications

References 128 publications

An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins

An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins

Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

Antagonists of Vitamin K—Popular Coumarin Drugs and New Synthetic and Natural Coumarin Derivatives

Contact Info

Product

Resources

About