Metal-free synthesis of carbamoylated dihydroquinolinones <i>via</i> cascade radical annulation of cinnamamides with oxamic acids

Suman, Pallav; Tomar, Kirti; Nishad, Chandra Shekhar; Banerjee, Biplab

doi:10.1039/d3ob01856c

Cited by 4 publications

(1 citation statement)

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“…Motivated by the above success, we became interested in extending this strategy to carbamoyl radicals generated from oxamic acids. 11 The reaction of biaryl enone 1a with oxamic acid 4a was selected as the model reaction for the optimization studies (for details, see the ESI†) and we found that the oxidant K 2 S 2 O 8 in the presence of Ag 2 CO 3 in acetonitrile gave the expected phenanthrenone 5a in 92% yield (Scheme 4). Having established the suitable reaction conditions, the substrate scope was then examined with a range of biaryl enones as well as oxamic acids.…”

Section: Resultsmentioning

confidence: 99%

Carbonylative cyclization of biaryl enones with aldehydes and oxamic acids

Reddy,

Kolgave,

Fatima

et al. 2024

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

Carbonylative cyclization of biaryl enones with aldehydes and oxamic acids

Reddy,

Kolgave,

Fatima

et al. 2024

Org. Biomol. Chem.

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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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One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium

Suresh,

Nawaz Khan

2024

ACS Omega

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The sequential synthesis of N-heterocycles from saturated ketones poses significant challenges and has rarely been reported. Herein, an efficient synthesis of alkenylated dihydroquinolinones 7 and hexahydroacridinones 8 is achieved from saturated ketones 1 or 2 via dehydrogenation, cyclization, oxidation, and αalkenylation in choline chloride-based deep eutectic solvent (DES) medium. This strategy provides alkenylated dihydroquinolinones 7 and hexahydroacridinones 8 in excellent yield from low-cost, readily available starting materials under environmentally benign conditions. Furthermore, the synthesized compounds (4, 5, 7, and 8) were investigated for their photophysical properties through absorption and emission spectral studies.

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Metal-free synthesis of carbamoylated dihydroquinolinones via cascade radical annulation of cinnamamides with oxamic acids

Abstract: We report a metal-free procedure for the sustainable synthesis of carbamoylated dihydroquinolinones via tandem addition-cyclization of carbamoyl radicals to cinnamamides. Readily accessible, non-toxic and inexpensive oxamic acids are used as...

Cited by 4 publications

References 75 publications

Carbonylative cyclization of biaryl enones with aldehydes and oxamic acids

Carbonylative cyclization of biaryl enones with aldehydes and oxamic acids

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

One-Pot Sequential Synthesis of Alkenylated Dihydroquinolinones and Hexahydroacridinones in Deep Eutectic Solvent Medium

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