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An Efficient Synthesis of 3‐Substituted Isoquinoline and Pyridine Derivatives by Gold Catalyzed Intramolecular Cyclization from o ‐Alkynyloximes
Author(s) -
Subbarao K. P. V.,
Reddy G. Raveendra,
Muralikrishna A.,
Reddy K. V.
Publication year - 2014
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2109
Subject(s) - chemistry , isoquinoline , pyridine , intramolecular force , benzene , naphthalene , medicinal chemistry , catalysis , nitrobenzene , toluene , organic chemistry
A one‐pot reaction was developed efficiently by AuCl 3 catalyzed intramolecular cyclization of aromatic o ‐alkynyloximes and 2‐alkynylcycloalkene‐1‐carbaldoximes leading to the formation of isoquinoline and pyridine derivatives with high yields. This methodology has been applied for aromatic as well as aliphatic systems. Aromatic o ‐alkynyloximes are benzene and naphthalene, whereas electron‐donating groups are 4‐methoxybenzene, 4‐methylbenzene, and 4‐methoxy‐5‐methylbenzene. There are electron‐withdrawing groups such as chloro and nitrobenzene o ‐alkynyl oximes, and the same methodology has been successfully applied to pyridine and piperonal, which is also extended to aliphatic rings such as five‐member, six‐member, seven‐member, and eight‐member 2‐alkynylcycloalkene‐1‐carbaldoximes.