Synthesis of a few cyclothiadiazanones and aminosulfonyl benzamides from saccharin

Saccharin is hydrolyzed with two different acids to yield 1,2-di-acid. The di-acid, on chlorination with phosphorous pentachloride, gave 2-chlorosulfonylbenzoyl chloride. The 2-chlorosulfonylbenzoyl chloride on hydrazinolysis gave benzothiadiazinetrione, while with phenyl hydrazine it selectively yi...

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Bibliographic Details
Published in:Journal of sulfur chemistry 2010-02, Vol.31 (1), p.71-81
Main Authors: Venkata Ramana, P., Ram Reddy, A.
Format: Article
Language:English
Subjects:
2-chlorosulfonylbenzoyl chloride
benzothiadiazepinone
dibenzothiadiazocine
hydrazine
phenylenediamine
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Summary:Saccharin is hydrolyzed with two different acids to yield 1,2-di-acid. The di-acid, on chlorination with phosphorous pentachloride, gave 2-chlorosulfonylbenzoyl chloride. The 2-chlorosulfonylbenzoyl chloride on hydrazinolysis gave benzothiadiazinetrione, while with phenyl hydrazine it selectively yielded 2-phenylbenzothiadiazinetrione. 2-chlorosulfonoylbenzoyl chloride with different aromatic 1,2-diamines resulted in dibenzothiadiazocine derivatives. Electron-donating groups in the diamine facilitate while the electron-withdrawing groups retard the cyclization. However, aliphatic diamines, aniline and substituted anilines readily gave acyclic aminosulfonyl carboxybenzamides on condensation with 2-chlorosulfonylbenzoyl chloride. The di-acid and anhydride did not react with either hydrazine/phenyl hydrazine or amines to give the above products. However, when its ester derivative, isopropyl-2-chlorosulfonylbenzoate, condensed with hydrazine, it gave benzothiadiazinetrione. But the ester failed to react with phenyl hydrazine. All the condensation reactions were carried out at room temperature.
ISSN:1741-5993
1741-6000
DOI:10.1080/17415990903480361