| Institution: | 1. Enamine Ltd., Chervonotkatska Street 78, Kyiv, 02094 Ukraine;2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv, 02094 Ukraine;3. Enamine Ltd., Chervonotkatska Street 78, Kyiv, 02094 Ukraine
Taras Shevchenko National University of Kyiv, Volodymyrska Street 64, Kyiv, 01601 Ukraine;4. Bienta/Enamine Ltd., Chervonotkatska Street 78, Kyiv, 02094 Ukraine;5. Chemspace, Ilukstes iela 38-5, Riga, 1082 Latvia |
| Abstract: | Two novel solid reagents—1-sulfonimidoyl- and 1-sulfamimidoyl-3-methylimidazolium derivatives—for the synthesis of sulfonimidamides and imidosulfuric diamides, respectively, were developed. It is shown that these reagents are very effective in substitution reactions with various N- and O-nucleophiles; therefore, they significantly extend the accessibility to the chemical space covered by organosulfur(VI) compounds with S=N bonds. In addition, previously unknown imidosulfuric diamides with free imino nitrogen groups were prepared, and their physical and chemical properties were characterized (including molecular geometry, pKa, Log P, microsomal stability, and reactivity towards typical electrophiles). Similar to other organosulfur(VI) derivatives with S=N bonds, these compounds can be considered as promising bioisosteres of amides, ureas, or sulfonamides. |
