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1.
Org Lett ; 26(7): 1416-1420, 2024 Feb 23.
Article in English | MEDLINE | ID: mdl-38329826

ABSTRACT

Despite the notable advancements made over the past decade in achieving carbon-carbon bonds by transition-metal-catalyzed cross-coupling processes, metal-free cross-coupling reactions for hydroacylation of aromatic alkynes via C(sp3)-H functionalization are still rare and highly desired. Here we report a metal-free reliable approach for the synthesis of α,ß-unsaturated ketones (chalcones) via C(sp3)-H functionalization using MeCN:H2O as green solvent, Eosin Y as organic photocatalyst, and ambient air as oxidant. More significantly, this strategy can effectively transform a variety of methyl arenes and aromatic alkynes into the desired product. With high atom efficiency, use of green solvents, metal-free nature, environmental friendliness, and visible light as a renewable energy source, this method is compatible with biologically active molecules.

2.
Chem Commun (Camb) ; 60(9): 1136-1139, 2024 Jan 25.
Article in English | MEDLINE | ID: mdl-38189089

ABSTRACT

The elucidation of the C-arylation of active methylene compounds under visible light conditions without a photocatalyst presents an intellectual challenge. The photo-induced C-arylation of active methylene compounds via electron donor-acceptor (EDA) complexes shows a strategic path for the synthesis of pharmacologically relevant compounds. This expansive and efficacious methodology facilitates C-arylation under environmentally conscientious conditions, exhibiting exemplary compatibility with diverse functional groups and yielding numerous compounds. This environmentally sustainable transformation underscores the merits of the procedural simplicity and benign reaction conditions. Notably, all resultant products were judiciously derived from active methylene compounds and diazonium salts through the intermediacy of the EDA complex.

3.
Org Biomol Chem ; 21(23): 4854-4862, 2023 Jun 14.
Article in English | MEDLINE | ID: mdl-37249156

ABSTRACT

A cost-effective and competent approach has been established for the synthesis of pyrimido[4,5-b]quinolines and pyrido[2,3-d]pyrimidines via a multicomponent reaction of 1,3 diketones (dimedone, barbituric acid, and Meldrum's acid), 6-aminouracil and aromatic aldehyde, through mechanochemical synthesis using a ball-mill. This transformation involves a one pot, catalyst-free, and solvent-free pathway to develop the desired products under mild reaction conditions.

4.
Chem Commun (Camb) ; 59(27): 4075-4078, 2023 Mar 30.
Article in English | MEDLINE | ID: mdl-36938640

ABSTRACT

An efficient C-N cross-coupling approach for the synthesis of hydrazones was developed through C(sp2)-H and C(sp3)-H functionalization of indole and methylarene under visible light irradiation using photocatalyst eosin Y, ethanol:water as a green solvent and atmospheric air as an oxidant. With the aid of eosin Y, the C-H bonds of indole and methylarenes were activated followed by coupling with arylhydrazines. The procedure was applied to a wide variety of substrates with good functional group compatibility, offering a creative way to make hydrazones from inexpensive and easily accessible raw materials. The absence of metals, low cost, environmental friendliness, green solvent, non-toxicity, ease of handling, and utilization of renewable energy sources like visible light are some of this method's primary advantages.

5.
Mol Divers ; 25(1): 131-142, 2021 Feb.
Article in English | MEDLINE | ID: mdl-31919739

ABSTRACT

A facile and efficient multicomponent synthesis of benzodiazepine ring in water under ultrasound irradiation is reported first time. The current procedure escapes traditional chromatography and purification process and provided the product in excellent yields of 95% as compared to conventional methods. The approach was also validated on gram-scale synthesis.


Subject(s)
Benzodiazepines/chemistry , Benzodiazepines/chemical synthesis , Water/chemistry , Ultrasonic Waves
6.
ACS Omega ; 5(46): 29854-29863, 2020 Nov 24.
Article in English | MEDLINE | ID: mdl-33251420

ABSTRACT

A comfortable, environment-friendly, and metal-free approach for synthesizing the biologically important moiety aminoimidazopyridine through the multicomponent reaction of benzylamine, 2-aminopyridine, and t-butyl isocyanide under visible light using eosin Y as a photocatalyst has been developed. Inexpensive, nontoxic, the effortless accessibility of starting materials, and nonparticipation of particular glassware and a photoreactor system are important qualities of the current approach. Strangely, the mild conditions, environment-friendly, and enumerating tolerance of an extensive range of both electron-donating and electron-withdrawing groups are additional features of the approach.

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