Summary.
The reaction of methyl saccharin-2-acetate with hydrazine gave no 3-hydrazino derivative of saccharin as reported in literature, but yielded with ring opening the benzohydrazide derivative. The analogue reaction was observed when saccharin-2-(2-propionate) was reacted with hydrazine. Furthermore, using an excess of hydrazine, the ester group was transformed into the carbohydrazide too. All hydrazides were fully characterized as hydrazones by reactions with different ketones. The 3-thioxo compounds were prepared by reactions with P2s5, but the yield was improved by using Lawesson’s reagent. No attack at the ester group was observed. Finally, reactions of the saccharin-2-carboxylate with some amino acids gave substituted benzamides by attack at position 3 and ring opening. In none of the reactions of the saccharin derivatives with nitrogen nucleophiles a formal substitution of the 3-oxo group was observed.
Similar content being viewed by others
Author information
Authors and Affiliations
Additional information
Corresponding author. E-mail: ottohh@pharmazie.uni-greifswald.de
Received July 4, 2002; accepted August 1, 2002 Published online February 20, 2003
Rights and permissions
About this article
Cite this article
Jarecka, D., Besch, A. & Otto, HH. On the Reaction of Some Saccharin Derivatives with Hydrazine and Other Nucleophils. Monatshefte füer Chemie 134, 901–908 (2003). https://doi.org/10.1007/s00706-002-0531-6
Issue Date:
DOI: https://doi.org/10.1007/s00706-002-0531-6