One-Pot 'On-solvent' Multicomponent Protocol for the Synthesis of Medicinally Relevant 4H-Pyrano[3,2-c]quinoline Scaffold

‘One‐pot’ AcONa‐catalyzed transformation of salicylaldehydes, malononitrile and 4‐hydroxy‐1‐methylquinolin‐2(1H)‐one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2‐amino‐4‐(2‐hydroxyaryl)‐6‐methyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline...

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Veröffentlicht in:Helvetica chimica acta 2015-08, Vol.98 (8), p.1104-1114
Hauptverfasser: Vereshchagin, Anatoly N., Elinson, Michail N., Nasybullin, Ruslan F., Ryzhkov, Fedor V., Bobrovsky, Sergey I., Bushmarinov, Ivan S., Egorov, Mikhail P.
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Sprache:eng
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Zusammenfassung:‘One‐pot’ AcONa‐catalyzed transformation of salicylaldehydes, malononitrile and 4‐hydroxy‐1‐methylquinolin‐2(1H)‐one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2‐amino‐4‐(2‐hydroxyaryl)‐6‐methyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline‐3‐carbonitriles in 85–98% yields, which are potential pharmaceutical agents for treating disorders responsive to the induction of apoptosis, antiproliferation, or vascular disruption. This efficient ‘on‐solvent’ approach to the 4H‐pyrano[3,2‐c]quinoline scaffold represents a novel synthetic concept for multicomponent reaction (MCR) strategy and allows to combine the synthetic virtues of conventional MCR with ecological benefits and convenience of facile ‘on‐solvent’ procedure.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201500026