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Gisbert, Patricia; Albert-Soriano, Maria; Pastor, Isidro M. published the article 《Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C-C and C-N Bond Formation》. Keywords: aminobenzaldehyde ketone biscarboxymethyl imidazolium chloride catalyst green tandem cyclization; quinoline preparation; aminoaryl ketone biscarboxymethyl imidazolium chloride catalyst green tandem cyclization; acridine preparation.They researched the compound: 2-Amino-5-chlorobenzaldehyde( cas:20028-53-9 ).Computed Properties of C7H6ClNO. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:20028-53-9) here.

Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Addnl., 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14-23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem