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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 22
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Articles

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

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Pages 3413-3423 | Received 27 Jun 2020, Published online: 07 Aug 2020
 

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

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.

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