Palladium-Catalyzed Domino Reaction for the Synthesis of 3-Amino 1,2,4-Benzothiadiazine 1,1-Dioxides

被引:4
作者
Hommelsheim, Rene [1 ]
van Nahl, Robin [1 ]
Hanek, Lena M. [1 ]
Ward, Jas S. [2 ]
Rissanen, Kari [2 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
[2] Univ Jyvaskyla, Dept Chem, Jyvaskyla 40014, Finland
关键词
Domino reactions; palladium catalysis; sulfur heterocycles; sulfonamides; azides; POTASSIUM CHANNEL OPENERS; BOND-DONATING ORGANOCATALYST; PANCREATIC B-CELLS; 3-ALKYLAMINO-4H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES; PHARMACOLOGICAL EVALUATION; BIOLOGICAL EVALUATION; FACILE SYNTHESIS; INSULIN-RELEASE; WITTIG REACTION; POTENT;
D O I
10.1002/adsc.202300875
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A palladium-catalyzed domino reaction of 2-azidosulfonamides and isocyanides enables the synthesis of 3-amino-substituted 1,2,4-benzothiadiazine 1,1-dioxides at room temperature. By applying commercially available Pd(dba)2 in catalyst loadings as low as 1.0 mol%, a variety of 21 differently substituted 2H-1,2,4-benzothiadiazine 1,1-dioxides can be prepared within 2 h. Moreover, the developed protocol gives access to the related 4H heterocycles. +image
引用
收藏
页码:717 / 724
页数:8
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