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Title
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One-pot sequential hydroamination protocol for N-heterocycle synthesis : one method to access five different classes of tri-substituted pyridines
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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The journal of organic chemistry. - Washington, D.C., 1936, currens
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Publication
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Washington, D.C.
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2023
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ISSN
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0022-3263
[print]
1520-6904
[online]
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DOI
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10.1021/ACS.JOC.2C02155
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Volume/pages
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88
:3
(2023)
, p. 1378-1384
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ISI
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000918863100001
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Pubmed ID
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36634317
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Full text (Publisher's DOI)
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