Generation of ArS- and ArSe-Substituted 4-Quinolone Derivatives Using Sodium Iodide As an Inducer

Abstract

An operationally simple sodium iodide-mediated C–S and C–Se bond formation protocol involving substituted 4-quinolone and thiols/diselenide to generate different ArS/ArSe-substituted 4-quinolone derivatives in excellent yields was developed. The versatility of this methodology has been successfully demonstrated by extension of the suitable reaction conditions to both substrates having different substituents. This regioselective C–H bond activation approach provides a direct access of structurally diverse 3-sulfenylated/selenylated 4-quinolone derivatives. Moreover, this new method proceeds without a transition-metal catalyst and prerequisite NH protection of 4-quinolone derivatives.

Atmospheric Oxygen Mediated Radical Hydrothiolation of Alkenes

“…Ap lethora of reagents andi nitiation strategies have been reportedfor the HAA step, with the photodecompositionofphotoinitiators under UV-mediatedc onditions frequently employed, as well as the generation of photoexcited metal complexesb yv isible light irradiation and electrochemical radical generation ( Figure 1a). [29][30][31][32][33][34][35][36][37][38][39][40][41][42][43] Furthermore, thermali nitiators may also be employed( Figure 1b). [44] In most instances external additives are required whicho ften demands trenuous work-up and purification for their removal.…”

Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

“…In addition, thiols can be replaced by amine and alcohol to afford the corresponding amines and ethers, respectively. In 2018, the Das group developed a C-H sulfenylation of 4-quinolones with thiols or disulfides in the presence of NaI and TBHP in DMSO (Scheme 28) [48]. The reactions of aryl thiols without a substituent at the para-position provided excellent yields while the reactions with para-substituted aryl thiols gave lower yields (about 60%).…”

Synthesis and Functionalization of 4‐Quinolones – A Progressing Story

“…A novel and operationally simple method reported by Das et al provides direct access to various S‐ and Se‐substituted quinolones by using NaI and TBHP to initiate the reaction of different 4‐quinolones with thiols/diselenide (Scheme ) . This protocol offers several advantages as it avoids the use of a transition metal catalyst and the ArS/ArSe derivatives are obtained in excellent yields.…”