Beilstein J. Org. Chem.2016,12, 1072–1078, doi:10.3762/bjoc.12.101
described. A range of electronically diverse acetophenones reacted well with several 2-aminobenzenesulfonamides, affording 3-acylbenzothiadiazine1,1-dioxides in good yields.
Keywords: 3-acylbenzothiadiazine1,1-dioxides; cyclization; metal-free; oxidation; Introduction
Benzothiadiazine 1,1-dioxide
of luotonin F and derivatives from aromatic ketones and 2-aminobenzamides via iodination/Kornblum oxidation/annulation [25]. We envisioned that 2-aminobenzenesulfonamides would undergo a similar reaction to afford 3-acylbenzothiadiazine1,1-dioxides. Herein, we report the first synthesis of 3
biologically active benzothiadiazine 1,1-dioxides.
Experimental
Typical procedure for the synthesis of 3-acylbenzothiadiazine1,1-dioxides: A mixture of acetophenone (0.040 mL, 0.33 mmol), I2 (0.057 g, 0.225 mmol) and 2-aminobenzenesulfonamide (0.051 g, 0.3 mmol) in DMSO (2 mL) was stirred at 110 °C under air
PDF
Graphical Abstract
Scheme 1:
Selected benzothiadaiazine 1,1-dioxides with potent biological activities.