Synthesis of Naphthalene Functionalized Trans‐2,3‐dihydrofuro[3,2‐c]coumarins as Antioxidant and Anthelmintic Agents

Abstract

A series of trans‐2,3‐dihydrofuro[3,2‐c]coumarins (4) has been synthesized by a one‐pot multicomponent reaction by aromatic aldehydes, 4‐hydroxycoumarin, α‐tosyloxyketones, and pyridine using triethylamine as catalysts in acetonitrile. The synthesized compounds were then screened for their antioxidant and anthelmintic activities.

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

“…They have antimicrobial, 11 antifungal, 12 antiinflammatory, 13 antitumor, 14 anti-HIV, 15 and anti-allergenic pharmacological activities (Figure 1). 16 In addition, they can be used to treat Alzheimer's disease, Parkinson's disease, Down syndrome, and schizophrenia. [17][18][19][20] Researchers have developed a variety of synthetic strategies using different substrates to obtain the special structure of 4H-pyrano [3,2c]coumarin and its derivatives.…”

Synthesis of furo[3,2-c]coumarins under microwave irradiation using nano-CoFe2O4@SiO2–PrNH2 as an efficient and magnetically reusable catalyst

“…Mp 234-244°C (mp 234°C (EtOH) 16,27 X-ray structural investigation of compound 4c was carried out on a Rigaku SuperNova automatic diffractometer (MoKα radiation, mirror monochromator, λ 0.71073 Å) at 150 K. Crystals suitable for single-crystal crystallography were produced by evaporation of a saturated solution of compound 4c in ethyl acetate. Unit cell information, intensity data and absorption corrections were obtained with the CrysAlis PRO software package.…”

Effective Synthesis and Biological Evaluation of Functionalized 2,3-Dihydrofuro[3,2-c]coumarins via an Imidazole-Catalyzed Green Multicomponent Approach

“…Moreover, great attention from researchers has been given to their organic synthesis, which has led to several elegant methodologies for their rapid construction and stimulated intense research activities toward their structural modification and biological evaluation. − Several syntheses of DHFCs in the literature reported the one-pot, tandem reaction of pyridinium ylide, 4-hydroxycoumarin, and aldehyde catalyzed by Et 3 N/DBU/pyridine or a mixture of AcOH and AcONH 4 to synthesize various fused 2,3-dihydrofuran derivatives including 2,3-dihydrofuro­[3,2- c ]­chromen-4-ones. In addition, Wadhwa et al developed the multicomponent reaction catalyzed by pyridine and Et 3 N in CH 3 CN to synthesize naphthalene-functionalized DHFC and featured its screening toward antioxidant and anthelmintic activities . Subsequently, the alternative pathway disclosed by Safaei-Ghomi et al, where MgO nanoparticles along with pyridine have been used as a catalyst for the diastereoselective preparation of DHFC under ultrasonic irradiation, and the method of Kamal et al (pyridine-catalyzed one pot synthesis) are well-described toward this end .…”

“…In addition, Wadhwa et al developed the multicomponent reaction catalyzed by pyridine and Et 3 N in CH 3 CN to synthesize naphthalene-functionalized DHFC and featured its screening toward antioxidant and anthelmintic activities. 33 Subsequently, the alternative pathway disclosed by Safaei-Ghomi et al, where MgO nanoparticles along with pyridine have been used as a catalyst for the diastereoselective preparation of DHFC under ultrasonic irradiation, and the method of Kamal et al (pyridine-catalyzed one pot synthesis) are well-described toward this end. 34 Alternatively, modified approaches by Kumar and group (HTIB, pyridine with Et 3 N, and CH 3 CN via in situ generated α-tosyloxyketones) and Samant et al [microwave-assisted, 4-dimethylaminopyridine (DMAP)-mediated multicomponent approach] have been reported.…”