On the Reaction of Some Saccharin Derivatives with Hydrazine and Other Nucleophils |
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Authors: | Danuta Jarecka Anita Besch Hans-Hartwig Otto |
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Institution: | (1) Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, D-17487 Greifswald, Germany, DE |
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Abstract: | 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.
Corresponding author. E-mail: ottohh@pharmazie.uni-greifswald.de
Received July 4, 2002; accepted August 1, 2002
Published online February 20, 2003 |
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Keywords: | , Saccharin derivatives, Hydrazine, Lawesson’,s reagent, Amino acids, |
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