2018
DOI: 10.1002/slct.201801799
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HKUST‐1‐Catalyzed Formation of C–C and C‐N Bonds: Rapid Assembly of Substituted Pyridines from Propargylamine and Carbonyl Compounds

Abstract: An efficient synthesis of 2,3‐fused pyridines through a HKUST‐1 (copper(II) 1,3,5‐benzenetricarboxylate) catalyzed sequential amination/annulation/aromatization reaction of carbonyl compounds and N‐propargylamine is presented herein. The reaction is not restricted to reactive ketones, wherein the five‐, six‐membered cyclic ketones and benzyl, aryl ketones show good reactivity with N‐propargylenamine, delivering pyridines in moderate to good yields. Under reaction conditions devoid of high temperature and expen… Show more

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Cited by 2 publications
(2 citation statements)
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“…Also, during our project, Meng and co-workers published a report, where copper­(II) 1,3,5-benzenetricarboxylate (HKUST-1) is used as the reaction catalyst but with the low scaling of the reaction (only up to ca. 500 mg of a ketone) . This report is consistent with our preliminary results on the catalytic synthesis of pyridines starting from propargylamine in the presence of HKUST-1 .…”
Section: Resultsmentioning
confidence: 99%
“…Also, during our project, Meng and co-workers published a report, where copper­(II) 1,3,5-benzenetricarboxylate (HKUST-1) is used as the reaction catalyst but with the low scaling of the reaction (only up to ca. 500 mg of a ketone) . This report is consistent with our preliminary results on the catalytic synthesis of pyridines starting from propargylamine in the presence of HKUST-1 .…”
Section: Resultsmentioning
confidence: 99%
“…At present, many of the methods available to prepare pyridines from non-activated ketones provide products bearing no further functionalisation ( i.e. positions 4–6 = H), 39–44 or bearing specific substituents and substitution patterns. 45–56 In the former case, an operationally straight-forward Au-catalysed annulation of unfunctionalised pyridine rings to ketones was described by Arcadi, which proceeded by reacting ketones with propargylamine (Scheme 3a).…”
Section: Annulation Of Unsaturated Nitrogen-containing Ringsmentioning
confidence: 99%