We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Sulfonimidamides and Imidosulfuric Diamides: Compounds from an Underexplored Part of Biologically Relevant Chemical Space.
- Authors
Zasukha, Sergiy V.; Timoshenko, Vadim M.; Tolmachev, Andrey A.; Pivnytska, Valentyna O.; Gavrylenko, Oleksii; Zhersh, Serhii; Shermolovich, Yuriy; Grygorenko, Oleksandr O.
- 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.
- Subjects
MOLECULAR shapes; DIAMIDES; IMINO group; SUBSTITUTION reactions; CHEMICAL properties; BIOISOSTERES
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 28, p6928
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201900440