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One‐Pot Synthesis of Naphtho[1′,2′:4,5]imidazo[1,2‐ a ]pyridin‐5‐yl(aryl)methanones through Sequential Sonogashira Coupling/Alkyne–Carbonyl Metathesis
Author(s) -
Baig Mirza Feroz,
Shaik Siddiq Pasha,
Krishmballa Hari,
Chouhan Neeraj Kumar,
Alarifi Abdullah,
Kamal Ahmed
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700496
Subject(s) - chemistry , sonogashira coupling , alkyne , aryl , moiety , metathesis , trifluoroacetic acid , medicinal chemistry , intramolecular force , pyridine , cycloalkane , stereochemistry , palladium , catalysis , organic chemistry , alkyl , polymer , polymerization
An efficient one‐pot route for the construction of naphtho[1′,2′:4,5]imidazo[1,2‐ a ]pyridin‐5‐yl(aryl)methanones and 5‐phenylnaphtho[1′,2′:4,5]imidazo[1,2‐ a ]pyridines by sequential Sonogashira coupling reaction followed by trifluoroacetic acid promoted alkyne‐carbonyl metathesis (ACM) has been developed. 2‐(2‐Bromophenyl)imidazo[1,2‐ a ]pyridine‐3‐carbaldehyde preferentially underwent ACM with phenyl acetylenes, whereas intramolecular hydroarylation reaction was the common pathway in the absence of a carbonyl moiety at the C‐3 position under similar conditions. This protocol is compatible with a wide variety of functional groups and delivered corresponding naphtho[1′,2′:4,5]imidazo[1,2‐ a ]pyridines in good to excellent yields.