Direct Introduction of Sulfonamide Groups into Quinoxalin‐2(1H)‐ones by Cu‐Catalyzed C3‐H Functionalization

Abstract

Direct sulfonamidation of quinoxalin-2(1H)-one derivatives has been developed using a readily available Cu salt as the catalyst and inexpensive ammonium persulfate as the oxidant in moderate conditions. Owing to the feature of handy operation and good functional group tolerance, this method provides a convenient and efficient access to curative 3-sulfonamidated quinoxalin-2(1H)-one scaffolds.

A novel cellulose/chitosan composite nanofiltration membrane prepared with piperazine and trimesoyl chloride by interfacial polymerization

“…With the polyethyleneimine/sulfonation of the polyethersulphone (PEI/SPES) composite nanofiltration membrane, 25 under the operating pressure of 0.4 MPa at room temperature, and a water flux of the PEI/SPES composite nanofiltration membrane at 5.8 L m −2 h −1 , the rejections to Na 2 SO 4 and NaCl were 29% and 18%, respectively. Compared to the PEI/SPES composite nanofiltration membrane, IP-BC/CS-NFM demonstrated better permeation and rejection.…”

Visible‐Light‐Induced Direct C−H Amination of Quinoxalin‐2(1H)‐ones

“…[12] In particular, 3-aminoquinoxalin-2(1H)-ones as an important subfamily has appeared in numerous bioactive compounds such as histamine-4 receptor antagonists, [13] modulator of PAS kinase, [14] ataquimast, [15] and epsteine-barr virus inhibitor (Figure 1). [16] In this context, the direct C(sp 2 )À H amination, [17] amidation, [18] and sulfonation [19] reactions of quinoxalin-2(1H)-ones using primary or secondary amines, amides and NH-sulfoximines as the effective amino source have been explored in recent years. Several outstanding progresses have been achieved by the groups of Cui, [17a] Qu, [18] Yotphan [19b] and et al In 2019, Zhang and co-workers introduced the amination of quinoxalin-2(1H)-ones with TMSN 3 to construct primary 3-aminoquinoxalin-2(1H)-ones by employing stoichiometric Ce(NH 4 ) 2 (NO 3 ) 6 as an oxidant (Scheme 1d).…”

Visible-light-photocatalysis driven denitrogenative/radical 1,3-shift of benzotriazole: access to 3-aryl-aminoquinoxalin-2(1H)-one scaffolds

“…Owing to their important synthetic value, not surprisingly, many efforts have been devoted to synthesizing 3-aminoquinoxalin-2(1 H )-one and its derivatives. Traditional synthetic methods are mainly dependent on transition metals, 6 stoichiometric oxidants 7 etc . 8 Despite their efficiencies, all these established approaches have encountered inherent drawbacks obviously, such as harsh reaction conditions, pre-functionalized starting materials and stoichiometric amounts of strong oxidants.…”