In situ synthesis of SO₃H supported Fe₃O₄@resorcinol–formaldehyde resin core/shell and its catalytic evaluation towards the synthesis of hexahydroquinoline derivatives in green conditions

Abstract

A novel core@double-shell acidic nanocatalyst (Fe3O4@SiO2@RF–SO3H) was prepared, characterized and applied in catalytic one-pot condensation between aromatic aldehydes, dimedone, malononitrile, and ammonium acetate for synthesis of hexahydroquinoline derivatives.

A eutectogels-catalyzed one-pot multi-component reaction: access to pyridine and chromene derivatives

“…52,56 Subsequently, an intramolecular cyclization mechanism ensues, leading to the formation of the intended product, pyridine IVa and chromene IIIb structure. 57,58 The formation of Va occurs via the anomericbased oxidation (ABO) mechanism, involving the elimination of a single water molecule. 59 The control reactions were also conducted to prove the reasonableness of the mechanism proposed.…”

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

“…[101] Instead of ethyl ethylacetoacetate, malononitrile can also be used for the synthesis of 1,4-dihydropyridine derivatives. [112][113][114] Recently, Mansoor and co-workers treated malononitrile with aromatic aldehydes, NH 4 OAc and cylohexane-1,3-diones for the synthesis of 2-amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives 6 applying Lewis acid character of Bi(NO 3 ) 3 .5H 2 O as a catalyst in ethanol solvent at 80 °C (Scheme 6). [115] They have also reported similar reaction earlier catalyzed by melamine trisulfonic acid under neat conditions.…”

Ionic liquid immobilized on modified magnetic FSM-16: an efficient and magnetically recoverable nanocatalyst

“…Polyhydroquinoline derivatives are usually synthesized via the four-compound one-pot reaction of aldehyde, dimedone, ethyl acetoacetate, ammonium acetate, and the corresponding catalyst. [49][50][51] In continuation of our studies program for the synthesis of novel heterogeneous nanocatalysts and also considering the importance of mesoporous materials in the catalysis synthesis process, 12,[52][53][54][55][56][57][58] herein, a recyclable magnetic catalyst based on FSM-16 (Fe 3 O 4 @FSM-16-SO 3 /IL) has been synthesized and characterized. Furthermore, Fe 3 O 4 @FSM-16-SO 3 /IL was used as an effective catalyst in the synthesis of polyhydroquinoline derivatives via the one-pot reaction of various aromatic aldehydes, dimedone, ethyl acetoacetate, and ammonium acetate.…”

“…Polyhydroquinoline derivatives are usually synthesized via the four-compound one-pot reaction of aldehyde, dimedone, ethyl acetoacetate, ammonium acetate, and the corresponding catalyst. 49–51…”