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 |
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creator | Elinson, Michail N. Gorbunov, Sergey V. Vereshchagin, Anatoly N. Nasybullin, Ruslan F. Goloveshkin, Alexander S. Bushmarinov, Ivan S. Egorov, Mikhail P. |
description | 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.
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doi_str_mv | 10.1016/j.tet.2014.09.066 |
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[Display omitted]</description><subject>Cascade reaction</subject><subject>Cascades</subject><subject>Chromeno[2,3-b]pyridines</subject><subject>Electrocatalysis</subject><subject>Electrolysis</subject><subject>Formations</subject><subject>Ligands</subject><subject>Malononitrile</subject><subject>Salicylaldehyde</subject><subject>Strategy</subject><subject>Tetrahedrons</subject><subject>Transformations</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kU2O1DAQhSMEEs3AAdh5yYKEcuwkbVih1vAjjcQGVghZjl1W3HLiYLsZhdUcA67CceYkuNWsWdWi3nv181XVcwoNBdq_OjYZc9MC5Q2IBvr-QbWjvOd1x2n_sNoBcKg5tPC4epLSEQAobdmu-nOYcHZaeaIWQ9CjzjFolZXfstNEq6SVQaI37d1PlV1YSLAkKe_05pU3OG2lfevyRPIUEckcSsbJYzrrZuXDEhaXo_P4mtzf_QoL1mvI93e_SXLz6vEy11qnHS6Z3KqN5FCyyswphhmX8LV9yerx27pFZ9yCpGxkbfDmafXIKp_w2b96VX15d_358KG--fT-4-HtTa0Zg1z37X4cBJhhPzBGNXTDqEfbg9AdHbUZsDNqz5VoRdfyFqzoSouxgQk1UgvArqoXl9w1hu8nTFnOLmn0Xi0YTknSgfN-4GJoi5RepDqGlCJauUY3q7hJCvLMSR5l4STPnCQIWTgVz5uLB8sNPxxGmc6v0GhcLDSkCe4_7r_ePaE7</recordid><startdate>20141111</startdate><enddate>20141111</enddate><creator>Elinson, Michail N.</creator><creator>Gorbunov, Sergey V.</creator><creator>Vereshchagin, Anatoly N.</creator><creator>Nasybullin, Ruslan F.</creator><creator>Goloveshkin, Alexander S.</creator><creator>Bushmarinov, Ivan S.</creator><creator>Egorov, Mikhail P.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20141111</creationdate><title>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</title><author>Elinson, Michail N. ; Gorbunov, Sergey V. ; Vereshchagin, Anatoly N. ; Nasybullin, Ruslan F. ; Goloveshkin, Alexander S. ; Bushmarinov, Ivan S. ; Egorov, Mikhail P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-628b790d787331c057bcbf609c51bcd7e5da84a92952420f9509c33739ab1f003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Cascade reaction</topic><topic>Cascades</topic><topic>Chromeno[2,3-b]pyridines</topic><topic>Electrocatalysis</topic><topic>Electrolysis</topic><topic>Formations</topic><topic>Ligands</topic><topic>Malononitrile</topic><topic>Salicylaldehyde</topic><topic>Strategy</topic><topic>Tetrahedrons</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Elinson, Michail N.</creatorcontrib><creatorcontrib>Gorbunov, Sergey V.</creatorcontrib><creatorcontrib>Vereshchagin, Anatoly N.</creatorcontrib><creatorcontrib>Nasybullin, Ruslan F.</creatorcontrib><creatorcontrib>Goloveshkin, Alexander S.</creatorcontrib><creatorcontrib>Bushmarinov, Ivan S.</creatorcontrib><creatorcontrib>Egorov, Mikhail P.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Elinson, Michail N.</au><au>Gorbunov, Sergey V.</au><au>Vereshchagin, Anatoly N.</au><au>Nasybullin, Ruslan F.</au><au>Goloveshkin, Alexander S.</au><au>Bushmarinov, Ivan S.</au><au>Egorov, Mikhail P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>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</atitle><jtitle>Tetrahedron</jtitle><date>2014-11-11</date><risdate>2014</risdate><volume>70</volume><issue>45</issue><spage>8559</spage><epage>8563</epage><pages>8559-8563</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><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 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.
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subjects | Cascade reaction Cascades Chromeno[2,3-b]pyridines Electrocatalysis Electrolysis Formations Ligands Malononitrile Salicylaldehyde Strategy Tetrahedrons Transformations |
title | 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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