Copper-catalyzed cascade syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing S and N atom respectively from AcSH and TsNH(2).
A copper-catalyzed cascade method has been developed to synthesize the 2H-benzo[b][1,4]thiazin-3(4H)-ones from 2-halo-N-(2-halophenyl)-acetamides 1 and AcSH via the S(N)2/deacetylation/coupling process, and to synthesize the quinoxalin-2(1H)-ones from 1 and TsNH(2) via the S(N)2/coupling/desulfonation process. The target products were obtained with diversity at three positions on their scaffolds.
Chen
Dingben
D
Department of Chemistry, Zhejiang University, Xi Xi Campus, Hangzhou 310028, Zhejiang, People's Republic of China.
Wang
Zhi-Jing
ZJ
Bao
Weiliang
W
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D015394:Molecular Structure; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013843:Thiazines / Q000138:chemical synthesis* / Q000737:chemistry; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry; D000096926:Benzenesulfonamides
D003300:Copper; D007202:Indicators and Reagents; D011810:Quinoxalines; D013449:Sulfonamides; D013843:Thiazines; D014050:Toluene; C025417:4-toluenesulfonamide; D000096926:Benzenesulfonamides