Transformation of 2H-1,2,3-benzothiadiazine 1,1-dioxides variously substituted at the aromatic ring, via nucleophilic substitution and demethylation reactions

Abstract

2H-1,2,3-Benzothiadiazine 1,1-dioxides are a class of compounds of pharmacological interest. After earlier studies carried out at our laboratory on various transformations (alkylation, acylation, and reduction) at the hetero ring, the present paper focuses on the transformation of substituents at the aromatic carbocycle, including nucleophilic substitution of chlorine atoms and demethylation of the methoxy group with amines. The new methods described here allow the introduction of versatile functional groups on the aromatic ring, making these compounds useful building blocks for organic and medicinal chemistry applications.

Graphical Abstract

Keywords:

• 2H-1,2,3-benzothiadiazine 1,1-dioxide
• SNAr
• amination
• demethylation
• NMR

Acknowledgments

We are thankful to Mr. Péter Kővágó, Dr. András Dancsó and Ms. Zsófia Garádi for the NMR and IR, Mrs. Mónika Mezővári and Dr. Róbert Kormány for the MS, to Dr. Mária Tóthné Lauritz, Ms. Dóra R. Németh, Mr. Ádám Veszely and Dr. Péter Slégel for the HRMS measurements.