Premium
HKUST‐1‐Catalyzed Formation of C–C and C‐N Bonds: Rapid Assembly of Substituted Pyridines from Propargylamine and Carbonyl Compounds
Author(s) -
Meng YanYu,
Kang WeiFen,
Si XiaoJu,
Song YuanYuan,
Li YanJie,
Xu Fen
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801799
Subject(s) - chemistry , aromatization , catalysis , amination , reactivity (psychology) , alkyl , annulation , aryl , medicinal chemistry , functional group , combinatorial chemistry , organic chemistry , polymer chemistry , polymer , medicine , alternative medicine , pathology
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 expensive catalyst, this method exhibits broad tolerance of functional groups, including CN, alkyl, benzyl and methoxy moieties as well as unprotected phenolic hydroxy group. Additionally, the role of organic link for HKUST‐1 has been considered as a key parameter for this transformation.