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Updated: May 13, 2026
Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction
Milena Trmčić1, Frances L Chadbourne, Paul M Brear
1Department of Chemistry, Science Laboratories, Durham University, South Road, Durham, DH1 3LE, United Kingdom.
Abstract:
We recently reported the use of PSCl3 for the thiophosphorylation of alkylamines where the resulting N-thiophosphoramidate ions could be readily S-alkylated (Chem. Commun., 2011, 47, 6156-6158.). Herein we report the development of this methodology using amino acid, amino sugar, aminonucleoside and aniline substrates. The hydrolysis properties of N-thiophosphoramidate ions and their reactivities towards alkylating agents are also explored. In addition, we demonstrate the application of our approach to the preparation of a small library of compounds, including quinoline-based N,S-dialkylthiophosphoramidates which were tested for antileishmanial activity.
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