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Synthesis 2018; 50(07): 1471-1481
DOI: 10.1055/s-0036-1591882
DOI: 10.1055/s-0036-1591882
paper
A Convenient Synthetic Approach to Saccharin Derivatives Containing a Sulfonylamidine Scaffold
Further Information
Publication History
Received: 10 November 2017
Accepted after revision: 04 December 2017
Publication Date:
11 January 2018 (online)
Abstract
A key intermediate was obtained as solid through filtration of the reaction mixture of saccharin, chloro(triphenyl)phosphonium chloride, and N,N-diisopropylethylamine (DIPEA) in chloroform. The soluble triphenylphosphine oxide went to filtrate as waste, while the solid was reacted with amines to afford N-sulfonylamidines. In total, 26 N-sulfonylamidine products were obtained in moderate to good overall yields.
Key words
amidine - N-sulfonylamidines - saccharin - chloro(triphenyl)phosphonium chloride - triphenylphosphine oxide - nucleophilic reaction - aza-pseudosaccharins - medicinal chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591882. Crystal data and experimental information of product 7, 1H NMR and 13C NMR spectra of the key intermediate mixture (13, 14) and final products are included.
- Supporting Information
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