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22.4.9.1.9.2 Method 2: Synthesis of N′′-Sulfonyl Carboximidohydrazides

DOI: 10.1055/sos-SD-022-00556

Ostrowska, K.; Kolasa, A.Science of Synthesis, (200522519.

Numerous publications describe the syntheses of open-chain,[‌329‌,‌382‌,‌411‌,‌436‌‌439‌] and semicyclic, derivatives of saccharin,[‌440‌‌447‌] or pyrazolone-5-imides,[‌448‌‌452‌] or cyclic alkyl or arylsulfonylated carboximidohydrazides.[‌366‌] The approaches used are based mainly on the reactions of N-sulfonylimidoyl chlorides[‌382‌,‌436‌,‌441‌,‌446‌] or N-sulfonylimidates[‌437‌,‌438‌,‌442‌,‌445‌] with hydrazines, or from the combination of imidates with N-(arylsulfonyl)hydrazines;[‌439‌] adaptations are employed to form semicyclic sulfonylated carboximidohydrazides. Other methods include the reactions of saccharin with hydrazine,[‌442‌,‌443‌] its hydrate [‌447‌] or N-isocyanamine,[‌444‌] the reaction of 3-methylsulfanyl-1,2-benzisothiazole 1,1-dioxide with hydrazine hydrate,[‌442‌] or the reactions of pyrazolone-5-imides with benzenesulfonyl chloride.[‌448‌‌450‌] Cyclic sulfonylcarboximidohydrazides can also be constructed using acetic anhydride as a carbon atom donor;[‌366‌] an extension of a general method for cyclic carbox­imidohydrazides described in Section 22.4.9.1.8.3. Examples of the synthetic procedures are illustrated in the reactions shown in Scheme 40, which lead to a range of sulfonylated carboximidohydrazides and related compounds 100106. Reviews of the stereochemistry[‌437‌] of sulfonylated carboximidohydrazides and their pharmacological activities[‌451‌,‌452‌] are available.

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