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- Title
One-Pot, Three-Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N-Sulfinyltritylamine, TrNSO.
- Authors
Davies, Thomas Q.; Hall, Adrian; Willis, Michael C.
- Abstract
Sulfonimidamides are increasingly important molecules in medicinal chemistry and agrochemistry, but their preparation requires lengthy synthetic sequences, which has likely limited their use. We describe a one-pot de novo synthesis of sulfonimidamides from widely available organometallic reagents and amines. This convenient and efficient process uses a stable sulfinylamine reagent, N-sulfinyltritylamine (TrNSO), available in one step on 10 gram scale, as a linchpin. In contrast to classical approaches starting from thiols or their derivatives, our TrNSO-based approach facilitates the rapid assembly of the three reaction components into a variety of differentially substituted sulfonimidamides containing medicinally relevant moieties, including pyridines and indoles. Analogues of the sulfonamide-containing COX-2 inhibitor Celecoxib were prepared and evaluated.
- Subjects
AMINES; CHEMICAL synthesis; CHEMICAL derivatives; PHARMACEUTICAL chemistry; ORGANOMETALLIC chemistry; CHEMICAL reagents
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 47, p15133
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201708590