Et<sub>3</sub>N‐ Promoted Cascade Sp<sup>3</sup> C‐H Bond Functionalization of Methyl Arene with Active Methylene CompoundsUnder Solvent‐Free Condition

An efficient synthesis of 3-functionalized coumarins is demonstrated from o-cresols and active methylene compounds under solvent-, metal-and catalyst-free conditions in the presence of 70 % aqueous tert-butyl hydrogen peroxide. The important features of this protocol are operational simplicity, mild reaction conditions and good to excellent yield of the products.Coumarin scaffold is well regarded parent compound present in several natural products and bioactive molecules. [1] Coumarin derivatives possess a wide range of biological activities including antibacterial, antifungal, anti-HIV, antioxidant, anticancer, analgesic and anti-inflammatory activities (Figure 1). [2] Coumarin scaffold also incorporated in insecticides, fragrances, perfumes, agrochemicals and used as additives in foods and cosmetics. [3] On the other hand, numerous coumarins compounds were explored as light-harvesting molecules, lightemitting diodes, triplet oxygen sensitizers, fluorescent probes, etc. [4] Hence, coumarin is very imperative building block for combinatorial library synthesis.Synthesis of these oxygen containing heterocyclic compounds usually executed by numerous methods including the von Pechmann, Knoevenagel, Perkin and Wittig reactions. [5,6] Knoevenagel condensation is not only an alternative, but also an efficient method for the synthesis of 3-substituted coumarins from salicylaldehyde with active methylene compounds like meldrum acid, malonate esters, ethyl cyanoacetate, etc. [6] Synthesis of 3-substituted coumarins via Knoevenagel condensation was achieved using different metal and metal-free catalyst like ZrCl 4 , MgÀ Al hydrotalcite, mesoporous molecular sieve MCM-41, p-toluenesulphonic acid, natural clay, PhI(OAc) 2 L-proline, NaOH, piperidine, MgFe 2 O 4 nanoparticles (Scheme 1, A). [1,5,6] However, most of these methods have their own merits and demerits.

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A Practical Synthesis of 3‐Functionalized Coumarins from o‐Cresols and Active Methylene Compounds under Metal and Catalyst‐Free Conditions Using tert‐Butyl Hydrogen Peroxide

Chauhan

Verma

Kandasamy

et al. 2020

ChemistrySelect

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Visible Light‐Induced Cu‐Catalyzed Synthesis of Schiff's Base of 2‐ Amino Benzonitrile Derivatives and Acetophenones

et al. 2021

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An efficient, mild, and environment‐friendly methodology for the synthesis of azomethine chromophores through the reaction of 2‐aminobenzonitrile derivatives and acetophenones has been developed using CuCl (10 mol %) catalyst and toluene as a solvent under visible light irradiation. The reaction proceeds readily at room temperature under 20 W white LED with good to excellent yields in short reaction time. This methodology shows significant advantages such as environmentally benign reaction conditions, sustainability, enumerating tolerance of wide range of functional groups, cost‐effectiveness, high atom economy, short reaction time, and applicability for large‐scale synthesis.

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Urea hydrogen peroxide-initiated synthesis of pyranopyrazoles through oxidative coupling under base- and metal-free conditions by physical grinding method

et al. 2021

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Et₃N‐ Promoted Cascade Sp³ C‐H Bond Functionalization of Methyl Arene with Active Methylene CompoundsUnder Solvent‐Free Condition

Cited by 5 publications

References 35 publications

A Practical Synthesis of 3‐Functionalized Coumarins from o‐Cresols and Active Methylene Compounds under Metal and Catalyst‐Free Conditions Using tert‐Butyl Hydrogen Peroxide

A Practical Synthesis of 3‐Functionalized Coumarins from o‐Cresols and Active Methylene Compounds under Metal and Catalyst‐Free Conditions Using tert‐Butyl Hydrogen Peroxide

Visible Light‐Induced Cu‐Catalyzed Synthesis of Schiff's Base of 2‐ Amino Benzonitrile Derivatives and Acetophenones

Urea hydrogen peroxide-initiated synthesis of pyranopyrazoles through oxidative coupling under base- and metal-free conditions by physical grinding method

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Et3N‐ Promoted Cascade Sp3 C‐H Bond Functionalization of Methyl Arene with Active Methylene CompoundsUnder Solvent‐Free Condition

Cited by 5 publications

References 35 publications

A Practical Synthesis of 3‐Functionalized Coumarins from o‐Cresols and Active Methylene Compounds under Metal and Catalyst‐Free Conditions Using tert‐Butyl Hydrogen Peroxide

A Practical Synthesis of 3‐Functionalized Coumarins from o‐Cresols and Active Methylene Compounds under Metal and Catalyst‐Free Conditions Using tert‐Butyl Hydrogen Peroxide

Visible Light‐Induced Cu‐Catalyzed Synthesis of Schiff's Base of 2‐ Amino Benzonitrile Derivatives and Acetophenones

Urea hydrogen peroxide-initiated synthesis of pyranopyrazoles through oxidative coupling under base- and metal-free conditions by physical grinding method

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Et₃N‐ Promoted Cascade Sp³ C‐H Bond Functionalization of Methyl Arene with Active Methylene CompoundsUnder Solvent‐Free Condition