One-Pot, Three-Component Sulfonimidamide Synthesis Exploiting the Sulfinylamine Reagent N -Sulfinyltritylamine, TrNSO

Autor:	Adrian Hall, Michael C. Willis, Thomas Q. Davies
Rok vydání:	2017
Předmět:	Sulfonamides Indoles Cyclooxygenase 2 Inhibitors Component (thermodynamics) Chemistry Pyridines 010405 organic chemistry One-pot synthesis General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis 0104 chemical sciences Celecoxib Reagent Organic chemistry Molecule Indicators and Reagents
Zdroj:	Angewandte Chemie. 129:15133-15137
ISSN:	0044-8249
DOI:	10.1002/ange.201708590
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7c2567276f59d6ba6a59c8e8077cb2bd https://doi.org/10.1002/ange.201708590 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.