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Acid‐Promoted Cascade Reaction of 4 H ‐Chromenes: Access to Hexahydronapthalenes via Decarboxylative Intramolecular Cyclization
Author(s) -
Kale Ashok,
Medishetti Nagaraju,
Babu Nanubolu Jagadeesh,
Atmakur Krishnaiah
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202004076
Subject(s) - chemistry , cascade reaction , intramolecular force , allene , yield (engineering) , alcohol , cascade , sulfonic acid , toluene , medicinal chemistry , combinatorial chemistry , reaction conditions , organic chemistry , catalysis , materials science , chromatography , metallurgy
Acid promoted cascade reaction of 4 H ‐chromenes with propargylic alcohol was described using p ‐toluene sulfonic acid ( p ‐TSA). The reaction proceeds through Meyer‐Schuster type of rearrangement of propargylic alcohol and subsequent reaction of 4 H ‐chromene with in situ generated allene followed by decarboxylative intramolecular cyclization leading to hexahydronapthalene scaffolds with good to excellent yield. Simple reaction conditions, high compatibility and excellent yields are the advantages of this protocol.