Synthesis and chlorinolysis of 2H-1,2,3-benzothiadiazine 1,1-dioxide

King, J. F.; Hawson, Anne; Deaken, Donna M.; Komery, J.

doi:10.1039/c29690000033

Cited by 14 publications

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“…This prompted us to carry out a comparatively detailed investigation of the course of this transformation and also a study of the chlorination of other sulfonhydrazones, to find out whether the reaction of 1 was typical or exceptional. Some of the earlier results in this study have been described in a preliminary communication (2).…”

mentioning

confidence: 66%

Chlorination of Heterocyclic and Acyclic Sulfonhydrazones

King¹,

Hawson²,

Huston³

et al. 1971

Can. J. Chem.

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Chlorination of 2H-1,2,3-benzothiadiazine 1,1-dioxide(1) in wet methylene chloride gives o-formylbenzenesulfonyl chloride (4), but in dry methylene chloride at 0° yields the chlorosultine 3-chloro-3H-2,1-benzoxathiole 1-oxide (2); the latter is readily hydrolyzed to the "pseudo-acid" 3H-2,1-benzoxathiol-3-ol 1-oxide (3) which on further chlorination forms 4. In 1,2-dichloroethane at −20° chlorination of 1 gave the "coupled product" 14, whereas in dimethylformamide at room temperature the cyclic acyl chloride hydrazone 4-chloro-2H-1,2,3-benzothiadiazine was isolated in poor yield. The acyl chloride hydrazones (16) were the products obtained following chlorination of some representative aromatic acyclic tosylhydrazones (15). 3H-2,3,4-Benzothiadiazepine2,2-dioxide (19), a previously unknown heterocyclic system, was synthesized in two steps from 1,3-dihydrobenzo[c]thiophene (17). Chlorinolysis of 19 gave o-chloromethylbenzal chloride (21). These reactions are believed to involve formation of the α-chloroazo compound (e.g. 22) as the first step. The formation of 2 from 1 is discussed in terms of three possible routes, two which involve the sulfene 23.

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mentioning

confidence: 66%

Chlorination of Heterocyclic and Acyclic Sulfonhydrazones

King¹,

Hawson²,

Huston³

et al. 1971

Can. J. Chem.

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“…The synthesis of the parent compound (1a) was first described by King et al in 1969, starting from sodium 2-formylbenzenesulfonate (2) via hydrazone 3 with erratic reproducibility and low yields (Scheme 1). Better results were obtained by changing the order of the two steps, i.e., by transformation of the sulfonate salt 2 to 2-formylbenzenesulfonyl chloride 4a and cyclization of the latter with hydrazine [13,14].…”

Section: Synthesis Of 4-unsubstituted 4-aryl and 4-alkyl Derivativesmentioning

confidence: 99%

Synthesis and Chemistry of 1,2,3-Benzothiadiazine 1,1-Dioxide Derivatives: A Comprehensive Overview

et al. 2020

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1,2,4-Benzothiadiazine 1,1-dioxide derivatives (e.g., chlorothiazide, hydrochlorothiazide) have been long used in the human therapy as diuretic and antihypertensive agents. Marketed drugs containing the structurally related phthalazinone scaffold are applied for the treatment of various diseases ranging from ovarian cancer to diabetes and allergy. 1,2,3-Benzothiadiazine 1,1-dioxides combine the structural features of these two compound families, which led to their more intensive research since the 1960s. In the present review, we summarize the literature of this period of more than half a century, including all scientific papers and patent applications dealing with the synthesis and reactions of this compound family, briefly hinting at their potential therapeutic application as well.

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“…Better results were obtained by changing the order of the two steps, i.e. by transformation of the sulfonate salt 4 to 2‐formylbenzenesulfonyl chloride 6 and the cyclization of the latter with hydrazine . The syntheses of key intermediate 4 were described in German patents more than hundred years ago, by treatment of 2‐chlorobenzaldehyde ( 7 ) with sodium bisulfite at high temperatures, or by oxidation of sodium ortho ‐toluenesulfonate ( 8 ) with manganese dioxide in oleum…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Alkylation and Reduction of 4‐Aryl‐2H‐1,2,3‐benzothiadiazine 1,1‐dioxides

et al. 2019

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ortho‐(2‐Aryl‐1,3‐dioxolan‐2‐yl)benzenesulfonyl chlorides obtained from benzophenone ketals by directed ortho‐lithiation chemistry were cyclized either with hydrazine monohydrate or with acetohydrazide to furnish variously substituted 4‐aryl‐2H‐1,2,3‐benzothiadiazine 1,1‐dioxides. Alkylation of benzothiadiazine dioxides with alkyl iodides under basic conditions was elaborated, revealing significant differences compared to the reactivity of 4‐unsubstituted ones. Hydrogenation of the C=N double bond in the presence of platinum(IV) oxide is also described. Detailed NMR studies and DFT calculations supported the structure elucidation of the compounds.

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Synthesis and chlorinolysis of 2H-1,2,3-benzothiadiazine 1,1-dioxide

Cited by 14 publications

References 0 publications

Chlorination of Heterocyclic and Acyclic Sulfonhydrazones

Chlorination of Heterocyclic and Acyclic Sulfonhydrazones

Synthesis and Chemistry of 1,2,3-Benzothiadiazine 1,1-Dioxide Derivatives: A Comprehensive Overview

Synthesis, Alkylation and Reduction of 4‐Aryl‐2H‐1,2,3‐benzothiadiazine 1,1‐dioxides

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