3-Arylsulfonylquinolines from N-Propargylamines via Cascaded Oxidative Sulfonylation Using DABSO

Abstract

We report a cascaded oxidative sulfonylation of Npropargylamine via a three-component coupling reaction using DABCO•(SO 2 ) 2 (DABSO). 3-Arylsulfonylquinolines were obtained by mixing diazonium tetrafluoroborate, N-propargylamine, and DABSO under argon atmosphere in dichloroethane (DCE) for 1 h. In a radical pathway, DABSO was utilized as the sulfone source and an oxidant in this radical-mediated cascaded reaction.

Visible light driven multicomponent synthesis of difluoroamidosulfonyl quinoline derivatives

“…Based on the above experimental observations and literature reports, 9,16 a possible radical mechanism is proposed.…”

“…15 In recent years, various reaction strategies have been developed for the preparation of C 3 -sulfonated quinolines from N -propargylanilines. 16 For example, Tang and co-workers demonstrated a cycloaddition reaction with aryl sulfonyl hydrazides as a sulfone source and TBHP as an oxidant for the synthesis of 3-arylsulfonylquinolines 16 a (Scheme 1a). Subsequently, Zhang and co-workers developed an eosin-Y-mediated visible-light photoredox-catalyzed sulfonylation of N -propargylanilines to access 3-arylsulfonylquinolines 16 b (Scheme 1b).…”

Selective Radical Transformations with Aryldiazonium Salts

“…Mal and co‐workers [54] published in 2022 a protocol for the cascade oxidative sulfonylation of N ‐propargylamine 55 with aryldiazonium salts 1 and DABSO 12 (Scheme 21). In their report, a three‐component one‐pot reaction furnished 3‐arylsulfonylquinoline motifs 56 after oxidation and aromatization.…”

[Au]-Catalyzed Cyclization of Propargyl-Tethered Ene-Amides: Substrate-Dependent Access to Tetrasubstituted Pyrroles, Aminophenols, and Dihydropyridines

“…Karunakar and co-workers utilized analogous substrates to isolate 1,4-oxazepines using catalytic AuCl 3 /AgSbF 6 ; Zora and co-workers synthesized substituted pyrroles via such 1,4-oxazepines by utilizing stoichiometric ZnCl 2 (Scheme c) . Balamurugan’s group utilized N -propargylic α-enamino esters to generate substituted pyridines using [Ag]-catalysis (Scheme d); a recent report by Mal and co-workers reported the synthesis of 3-arylsulfonylquinolines from N -propargyl amines using DABSO . An earlier work by Cacchi et al employed a CuBr-catalyzed reaction of N -propargylic enaminones to obtain substituted pyridines; however, the use of Cs 2 CO 3 in the absence of CuBr gave the pyrrole products .…”