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

Imre Gyűjtő; Márta Porcs-Makkay; Ernák Ferenc Várda; Gyöngyvér Pusztai; Gábor Tóth; Gyula Simig; Balázs Volk

doi:10.3762/bxiv.2020.73.v1

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

Imre Gyűjtő ,
Márta Porcs-Makkay ,
Ernák Ferenc Várda ,
Gyöngyvér Pusztai ,
Gábor Tóth ,
Gyula Simig and
Balázs Volk

Submitting author affiliation:

Egis Pharmaceuticals Plc., Budapest, Hungary

Beilstein Arch. 2020, 202073. https://doi.org/10.3762/bxiv.2020.73.v1

Published 16 Jun 2020

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

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, reduction) at the hetero ring, the present manuscript 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.

Keywords: 2H-1,2,3-benzothiadiazine 1,1-dioxide; S_NAr; amination; demethylation; debenzylation; NMR

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Gyűjtő, I.; Porcs-Makkay, M.; Várda, E. F.; Pusztai, G.; Tóth, G.; Simig, G.; Volk, B. Beilstein Arch. 2020, 202073. doi:10.3762/bxiv.2020.73.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)