One‐Pot ‘On‐solvent’ Multicomponent Protocol for the Synthesis of Medicinally Relevant 4H‐Pyrano[3,2‐c]quinoline Scaffold |
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| Authors: | Anatoly N. Vereshchagin Michail N. Elinson Ruslan F. Nasybullin Fedor V. Ryzhkov Sergey I. Bobrovsky Ivan S. Bushmarinov Mikhail P. Egorov |
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| Affiliation: | 1. N.?D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, RU‐119991 Moscow, (phone: +7‐499‐137‐38‐42;2. fax: +7‐499‐135‐53‐28);3. A.?N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, RU‐119991 Moscow |
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| Abstract: | ‘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. |
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| Keywords: | ‘ On‐solvent’ process Salicylaldehydes Malononitrile Quinolin‐2(1H)‐one, 4‐hydroxy‐1‐methyl‐ 4H‐Pyrano[3,2‐c]quinolines Multicomponent reactions (MCRs) |
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