Publication
Title
One-pot sequential hydroamination protocol for N-heterocycle synthesis : one method to access five different classes of tri-substituted pyridines
Author
Abstract
Tri-substituted pyridines are important scaffolds that can be found in a plethora of commercially available drugs. A one-pot general method for the selective synthesis of less explored/challenging patterns of tri-substituted pyridines is described. Hydroamination of alkynes with commercially available N-triphenylsilylamine generates N-silylenamines. These in situ generated N-silylenamines, upon reaction with α,β-unsaturated carbonyl compounds and subsequent oxidation, furnish 25 examples of selectively substituted 2,4,5-, 2,3,4-, 3,4,5-, 2,3,5-, and 2,3,6-trisubstituted pyridines in up to 78% yield. The reaction features high functional group compatibility providing an expeditious and general approach for the assembly of selectively substituted tri-substituted pyridine derivatives. The robustness and practicality of the reaction have been demonstrated in a gram-scale reaction.
Language
English
Source (journal)
The journal of organic chemistry. - Washington, D.C., 1936, currens
Publication
Washington, D.C. : 2023
ISSN
0022-3263 [print]
1520-6904 [online]
DOI
10.1021/ACS.JOC.2C02155
Volume/pages
88 :3 (2023) , p. 1378-1384
ISI
000918863100001
Pubmed ID
36634317
Full text (Publisher's DOI)
UAntwerpen
Research group
Publication type
Subject
External links
Web of Science
Record
Identifier
Creation 20.10.2023
Last edited 21.10.2023
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