Visible-Light-Mediated, Organophotocatalytic C–H Thiocyanation of Pyrazolo[1,5-a]pyrimidines DOI
Paramita Pattanayak,

Appanapalli N. V. Satyanarayana,

Tanmay Chatterjee

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13215 - 13223

Published: Sept. 11, 2024

Herein, we report a metal-free, organophotoredox-catalyzed sustainable C-H thiocyanation of biologically active class N-heterocycles, pyrazolo[1,5-

Language: Английский

HFIP-Mediated, Regio-, and Stereoselective Hydrosulfenylation of Ynamides: A Versatile Strategy to Access Ketene N,S-Acetals DOI Creative Commons

Appanapalli N. V. Satyanarayana,

Paramita Pattanayak, Tanmay Chatterjee

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Herein, we report an HFIP-mediated, versatile, sustainable, atom-economical, and regio- stereoselective hydro-functionalization of ynamides with various S-nucleophiles (1 equiv.) such as thiols, thiocarboxylic acids, carbamates, xanthates, O,O-diethyl S-hydrogen phosphorothioate to access a wide variety stereodefined trisubstituted ketene N,S-acetals under mild conditions. This protocol requires only HFIP, which plays multiple roles, acting Brønsted acid protonate the ynamide regioselectively at beta carbon generate reactive keteniminium intermediate, stabilizing intermediate solvent through H-bonding. After nucleophilic attack S-nucleophile on deprotonation, HFIP is regenerated in most cases can be easily recovered recycled, revealing high sustainability protocol. Remarkably, all reactions are highly efficient furnish excellent yields many pure products were obtained just by washing crude reaction mixture pentane. Significantly, green chemistry metrics found excellent.

Language: Английский

Citations

0
Metal-free iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water DOI

Guiting Peng,

Fang Wei, Jiang Bai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We report a metal-free iodosulfonylation of alkynes in water at room temperature, which efficiently produces ( E )-β-iodovinyl sulfones good to excellent yields with high regio- and stereoselectivity.

Language: Английский

Citations

0
Catalyst- and chromatography-free multi-component domino synthesis of 5-alkyl barbituric acids at room temperature DOI

Biswajita Baruah,

Monoj Sarma,

Gaurav Rastogi

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(13), P. 1051 - 1059

Published: June 22, 2024

5-Alkylated barbituric acids are an important class of compounds that constitute the basic moiety several clinically used hypnotic drugs. Here we report a catalyst-free domino Knoevenagel-Michael addition involving acid, aldehyde, and N,N-disubstituted aniline in solvent acetonitrile to synthesize 5-alkylated acid derivatives (72–94% yield) without using any chromatographic separation techniques. The C-4 position acts as Michael donor. All reactions successfully performed catalysts, providing environment-friendly economical route for synthesis. Moreover, less sensitive air moisture unlike many metal with easy products, simple operating procedures there is no need catalyst weighing, recovery, removal. A plausible mechanism also proposed based on control experiments.

Language: Английский

Citations

2
Visible-Light-Mediated, Organophotocatalytic C–H Thiocyanation of Pyrazolo[1,5-a]pyrimidines DOI
Paramita Pattanayak,

Appanapalli N. V. Satyanarayana,

Tanmay Chatterjee

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13215 - 13223

Published: Sept. 11, 2024

Herein, we report a metal-free, organophotoredox-catalyzed sustainable C-H thiocyanation of biologically active class N-heterocycles, pyrazolo[1,5-

Language: Английский

Citations

1