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Synthesis of 3‐Keto Pyridines from the Conjugated Allenone – Alkynylamine Oxidative Cyclization Catalyzed by Supported Au Nanoparticles
Author(s) -
Fragkiadakis Michael,
Kidonakis Marios,
Zorba Leandros,
Stratakis Manolis
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901451
Subject(s) - chemistry , aromatization , dehydrogenation , catalysis , conjugated system , pyridine , propargyl , oxidative phosphorylation , combinatorial chemistry , nanoparticle , medicinal chemistry , organic chemistry , nanotechnology , polymer , biochemistry , materials science
Abstract Recyclable supported Au nanoparticles on TiO 2 catalyze the cyclization of N ‐propargyl or N ‐homopropargyl β‐enaminones followed by dehydrogenation (aromatization) leading to substituted 3‐keto pyridines or 4‐picolines in very good yields. This pathway is in contrast to their known cyclization in the presence of Au(I) or Au(III) catalysts which provides 1,4‐oxazepines, instead. The enaminones are formed in situ upon mixing a conjugated allenone or allenyl ester with the alkynylamine, thus the pyridine‐forming transformation is typically a one pot process.