Chemical and electrocatalytic cascade cyclization of salicylaldehyde with three molecules of malononitrile: ‘one-pot’ simple and efficient way to the chromeno[2,3-b]pyridine scaffold |
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Authors: | Michail N Elinson Sergey V Gorbunov Anatoly N Vereshchagin Ruslan F Nasybullin Alexander S Goloveshkin Ivan S Bushmarinov Mikhail P Egorov |
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Institution: | 1. N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, 119991 Moscow, Russia;2. A.N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, 119991 Moscow, Russia |
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Abstract: | А new type of catalytic cascade cyclization was found: the direct ‘one-pot’ simple and efficient transformation of salicylaldehyde and three molecules of malononitrile into the chromeno2,3-b]pyridine systems. Chemical and electrochemical methods result in direct ‘one-pot’ formation of chromeno2,3-b]pyridines in 60–90% yields. The implication of electrocatalysis in complex cascade cyclization reaction is an efficient approach to medicinally relevant chromeno2,3-b]pyridines—the promising small-molecule ligands with pronounced antihistamic, antirheumatic and antiasthmatic activities. The electrocatalytic method is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast efficient and environmentally benign synthetic concept for cascade reactions strategy. |
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Keywords: | Cascade reaction Electrolysis Electrocatalysis Salicylaldehyde Malononitrile Chromeno[2 3-b]pyridines |
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