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Please login to access the full content or check if you have access via22.4.9.1.9.2 Method 2: Synthesis of N′′-Sulfonyl Carboximidohydrazides
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Ostrowska, K.; Kolasa, A., Science of Synthesis, (2005) 22, 519.
Numerous publications describe the syntheses of open-chain,[329,382,411,436–439] and semicyclic, derivatives of saccharin,[440–447] or pyrazolone-5-imides,[448–452] 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.[448–450] 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 100–106. Reviews of the stereochemistry[437] of sulfonylated carboximidohydrazides and their pharmacological activities[451,452] are available.
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References
| [329] | Meeee, M.; Meeeeeeeee, M.; Meeee, M., Meee. Meee. Meee., (8888) 88, 888. |
| [366] | ee Meeeee, M.; Meeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeeee, M.-M.; Meeeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
| [382] | Meeeee, M.; Meeeeee, M. M., M. Meee. Mee. M, (8888), 8888. |
| [411] | Meeeeeeeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeee, M.; Meeeee, M.; Meeeee-Meee, M., Mee. M. Meee., (8888) 88, 8888. |
| [436] | Meee, M.; Meeeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 8888. |
| [437] | Meeeeeee, M.; Meeeeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [438] | Meeeeeee, M.; Meeeeeeeeee, M., Meee Meee. Meeee., Mee. M, (8888) 88, 888. |
| [439] | Meee, M. M.; Meeee, M., M. Meee. Mee., (8888), 8888. |
| [440] | Meeeeeee, M., M. Meeee. Meee., (8888) 88, 888. |
| [441] | Meeeeeee, M. M.; Meeeeeeee, M. M.; Meee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [442] | Meeeeeeee, M. M.; Meeeeeee, M. M.; Meee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [443] | Mee, M., Meeeeee. Meee., (8888) 88, 8888. |
| [444] | Müeeee, M.; Meeeeeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888), 888. |
| [445] | Meee, M. M.; Meee, M. M.; Meeeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
| [446] | Meeee, M.; Meeeeeeee, M. M.; MeMee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [447] | Meeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meeeee Meee. Mee., (8888) 88, 888. |
| [448] | Meeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
| [449] | Meeeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
| [450] | Meeeeeeee, M.; Meeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
| [451] | Meeeee, M.; Meüeee-Meeeeee, M., Meeeeee.-Meeeee., (8888) 88, 8888. |
| [452] | Meee, M.; Meeeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
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