Visible-light-driven site-selective alkylation of the benzo core of coumarins

Singh, Ravi P.; Tripathi, Krishna N.; Singh, Shashank; Akhtar, Naved; Manna, Kuntal

doi:10.1039/d2cc03073j

Cited by 8 publications

(1 citation statement)

References 47 publications

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“…24 Compounds 1 and 3 are already described in the literature. 30,31 Absorption data for HDMI 4 have been reported. 32 General procedure for the synthesis of derivatives 1-3…”

Section: Methodsmentioning

confidence: 99%

Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Stoerkler,

Ulrich,

Retailleau

et al. 2024

Chem. Sci.

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“…24 Compounds 1 and 3 are already described in the literature. 30,31 Absorption data for HDMI 4 have been reported. 32 General procedure for the synthesis of derivatives 1-3…”

Section: Methodsmentioning

confidence: 99%

Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Stoerkler,

Ulrich,

Retailleau

et al. 2024

Chem. Sci.

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Visible‐Light Induced Selective C−H Arylation of 2‐Imino‐2H‐Chromene‐3‐Carbonitriles and Decarboxylative Ipso‐Arylation of 2‐Oxo‐2H‐Chromene‐3‐Carboxylic Acids

Sahoo,

Banik,

Vijaya Prasanna

et al. 2024

ChemPhotoChem

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Visible‐light induced selective arylation of 2‐imino‐2H‐chromene‐3‐carbonitriles and the decarboxylative ipso‐arylation of coumarin‐3‐carboxylic acids have been accomplished under mild conditions in the absence of either a base or an acid and an oxidant. By employing blue LEDs as an excitation source, the aryl radicals are generated by Ru(II) complex through a single‐electron transfer process, which subsequently react with 2‐imino‐2H‐chromene‐3‐carbonitriles and 2‐oxo‐2H‐chromene‐3‐carboxylic acids to produce the desired products. This is the first report on the selective arylation of conjugated systems without using either an acid or a base.

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Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides

Mondal,

Sati,

Hashim

et al. 2024

J. Org. Chem.

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A metal-free process has been developed for the sustainable synthesis of medicinally important sulfonylureas in one pot via the direct reaction of sulfonamides with amides in green solvent (DMC). The reaction proceeded efficiently at room temperature, and the products were obtained in good to excellent yields. The use of readily accessible, inexpensive, and environmentally benign starting materials and reagents, metal-free mild reaction conditions, wide substrate scope, tolerance to air and moisture, operational simplicity, and good atom economy are the salient features of this reaction protocol. Gram-scale synthesis of antidiabetic drugs tolbutamide and chlorpropamide in excellent yields further revealed the practical utility of this procedure. Additionally, the synthetic value of this straightforward method is showcased by the late-stage modification of drug molecules, including drug−drug conjugation with good yields. Preliminary mechanistic studies indicated the in situ generation of an isocyanate intermediate, which further reacts with sulfonamide to form sulfonylurea. As compared to other related methods reported for sulfonylurea synthesis, the current method obviates the requirement of traditional multistep protocols involving isolation of hazardous isocyanates and avoids the use of toxic phosgene.

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Visible-light-driven site-selective alkylation of the benzo core of coumarins

Abstract: An unprecedented, straightforward photochemical platform for efficient site-selective C-H alkylation of C7 position of benzocore via the cross coupling between coumarins and NHPI ester, employing Ru(II) as photocatalyst in visible...

Cited by 8 publications

References 47 publications

Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Experimental and theoretical comprehension of ESIPT fluorophores based on a 2-(2′-hydroxyphenyl)-3,3′-dimethylindole (HDMI) scaffold

Visible‐Light Induced Selective C−H Arylation of 2‐Imino‐2H‐Chromene‐3‐Carbonitriles and Decarboxylative Ipso‐Arylation of 2‐Oxo‐2H‐Chromene‐3‐Carboxylic Acids

Metal-Free Synthesis of Pharmaceutically Relevant Sulfonylureas via Direct Reaction of Sulfonamides with Amides

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