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Controlled One‐Pot Synthesis of Multiple Heterocyclic Scaffolds Based on an Amphiphilic Claisen‐Schmidt Reaction Intermediate
Author(s) -
Song Rong,
Yu Hui,
Huang Haowen,
Chen Yun
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904110
Subject(s) - amphiphile , chemistry , schmidt reaction , claisen rearrangement , combinatorial chemistry , solvent , selectivity , organic chemistry , aqueous solution , catalysis , polymer , copolymer
An efficient one‐pot synthesis method for multiple heterocyclic scaffolds was carried out based on the cyano‐containing amphiphilic Claisen‐Schmidt reaction intermediate. Several valuable heterocyclic compounds including isoindolinone, flavonoid and isobenzofuranone were conveniently synthesized from o‐cyanobenzaldehyde and o‐hydroxyacetophenone by controlling the reaction temperature, catalyst and solvent. In addition, a density functional theory (DFT) based calculation was carried out on the key amphiphilic intermediate for understanding the reaction selectivity in water and non‐aqueous solution.