3‐Carboxy‐/3‐Aminobicyclopentane‐Derived Sulfonamides and Sulfonyl Fluorides – Advanced Bifunctional Reagents for Organic Synthesis and Drug Discovery

A convenient approach to 1,3‐bifunctional sulfonyl fluorides, sulfonamides and sulfinates bearing a bicyclo[1.1.1]pentane unit attached to the sulfur atom and (protected) amino or carboxyl group is described. The method relied on photochemical decomposition of Barton [1‐hydroxypyridine‐2(1H)‐thione]...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-04, Vol.2020 (15), p.2210-2216
Main Authors: Kokhan, Serhii O, Valter, Yevheniia B, Tymtsunik, Andriy V, Komarov, Igor V, Grygorenko, Oleksandr O
Format: Article
Language:English
Subjects:
Carboxyl group
Carboxylic acids
Esters
Fluorides
Oxidation
Reagents
Sulfonamides
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Description
Summary:A convenient approach to 1,3‐bifunctional sulfonyl fluorides, sulfonamides and sulfinates bearing a bicyclo[1.1.1]pentane unit attached to the sulfur atom and (protected) amino or carboxyl group is described. The method relied on photochemical decomposition of Barton [1‐hydroxypyridine‐2(1H)‐thione] esters of the corresponding carboxylic acids as the key step, followed by oxidation and cleavage of the 2‐pyridyl moiety. The title building blocks were obtained on a gram scale, and their utility was demonstrated by preparation of an isosteric analogue of classical sulfonamide anitibiotic sulfanilamide, as well as some other common chemical modifications.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000303