Sulfonylacetonitriles as Building Blocks in Copper‐Catalyzed Domino Reactions: An Efficient Apporach to Sulfonated Isoquinolin‐1(2H)‐ones

Abstract

A simple and practical copper-catalyzed one pot synthesis of C-4 sulfonated isoquinolin-1(2H)-ones has been developed. To the best of our knowledge, this is the first example for the synthesis of sulfone-containing heterocycles through transition-metal-catalyzed Ullmann-type coupling reactions using sulfonylacetonitriles as the sulfonylating agents.[a] Q.

Ni/Pd-catalyzed Suzuki–Miyaura cross-coupling of alcohols and aldehydes and C–N cross-coupling of nitro and aminesviadomino redox reactions: base-free, hydride acceptor-free

“…The construction of eight-membered cyclic diaryl suldes via the domino reaction of arynes with thioaurone analogues, 4 toluene oxidation-Knoevenagel-condensation domino reaction, 5 Cu-catalyzed aryl-I bond thiolation for the switchable synthesis of 2,3-dihydrobenzothiazinones and benzoisothiazolones, 6 Cu-catalyzed one-pot synthesis of C-4 sulfonated isoquinolin-1(2H)-ones, 7 and Co-catalyzed diastereoselective diuoroalkylation/Giese addition domino reactions 8 are some of the recently reported applications of the domino approach in organic synthesis. Previously, Chandra et al reviewed the application of domino reactions in catalytic C-C bond formation.…”

Visible-Light-Initiated Cross-Dehydrogenative Coupling of Quinoxalin-2(1H)-ones and Simple Amides with Air as an Oxidant

“…Quinoxalin-2­(1 H )-ones are significant N-heterocycle motifs − existing in a wide variety of biologically active compounds, and tremendous efforts have been dedicated in recent few years to prepare structurally diverse quinoxalin-2­(1 H )-ones. Particularly, plenty of novel protocols for the synthesis of various C-3-functionalized quinoxalin-2­(1 H )-ones have been well developed, which include C3-selective alkylation, − alkoxylation, − acylation, − arylation, − amidation, amination, − trifluoromethylation, , phosphonation reactions, − and so forth. − So far, only one example of direct C­(sp 2 )–H/C­(O)­N–H amidation of quinoxalin-2­(1 H )-ones with various amides was reported by Mao and Yuan (Scheme a) .…”

C(sp2)–H/O–H cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with alcohols under visible-light photoredox catalysis

“…Quinoxalin-2(1H)-ones are prevalent nitrogen-heterocyclic units [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] in a broad range of pharmaceutically and biologically active compounds [19,20]. As a consequence, the development of novel synthetic protocols for the facile diversification of quinoxalin-2(1H)-one has been actively explored over the past few years [21].…”