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Use of Mesoporous Molecular Sieves in the Production of Fine Chemicals: Preparation of Dihydroquinolinones of Pharmaceutical Interest From 2′‐Aminochalcones
Author(s) -
Climent María J.,
Corma Avelino,
Iborra Sara,
Martí Laura
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201501403
Subject(s) - catalysis , mesoporous material , chemistry , molecular sieve , heterogeneous catalysis , yield (engineering) , adsorption , intramolecular force , aryl , organic chemistry , solvent , combinatorial chemistry , chemical engineering , materials science , alkyl , engineering , metallurgy
Solid catalysts can be an alternative to homogeneous mineral Brønsted and Lewis acids for the synthesis of pharmaceuticals provided that the diffusional and adsorption properties of the reactants and products can be controlled. Structured micro and especially monolayered zeolites and mesoporous materials can be active and selective for intramolecular cyclization reactions and, more specifically, for intramolecular aza‐Michael cyclizations of 2′‐aminochalcones to yield aryl‐2,3‐dihydro‐4(1 H )‐quinolinones of pharmaceutical interest. However, the catalyst deactivates by strong adsorption of the basic quinolinone product. Product desorption has been controlled by optimizing catalyst pore structure and surface composition, together with a proper selection of solvent and reaction temperature. Process intensification for the synthesis of aryl‐2,3‐4(1 H )‐quinolinones of pharmaceutical interest has been achieved by preparing catalysts that allow the one‐pot synthesis of the dihydroquinolinones starting from 2′‐nitrochalcones with excellent yields.