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

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 chromeno[2,3-b]pyridine systems. Chemical and electrochemical methods result in direct ‘one-pot’ formation of chromeno[2,3-...

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Veröffentlicht in:Tetrahedron 2014-11, Vol.70 (45), p.8559-8563
Hauptverfasser: Elinson, Michail N., Gorbunov, Sergey V., Vereshchagin, Anatoly N., Nasybullin, Ruslan F., Goloveshkin, Alexander S., Bushmarinov, Ivan S., Egorov, Mikhail P.
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Sprache:eng
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Zusammenfassung: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 chromeno[2,3-b]pyridine systems. Chemical and electrochemical methods result in direct ‘one-pot’ formation of chromeno[2,3-b]pyridines in 60–90% yields. The implication of electrocatalysis in complex cascade cyclization reaction is an efficient approach to medicinally relevant chromeno[2,3-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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.09.066