Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters
An efficient iodine‐catalyzed three‐component Mannich‐type reaction of various 2‐alkylfurans, methyl 2‐formylbenzoates and carbamates under mild reaction conditions was realized. Synthetic utility of the resulting N‐Boc‐1‐[2‐(carbomethoxy)aryl]furfurylamines was demonstrated by their facile two‐step...
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| Veröffentlicht in: | European journal of organic chemistry 2018-01, Vol.2018 (4), p.461-469 |
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| container_title | European journal of organic chemistry |
| container_volume | 2018 |
| creator | Shpuntov, Pavel M. Kolodina, Alexandra A. Uchuskin, Maxim G. Abaev, Vladimir T. |
| description | An efficient iodine‐catalyzed three‐component Mannich‐type reaction of various 2‐alkylfurans, methyl 2‐formylbenzoates and carbamates under mild reaction conditions was realized. Synthetic utility of the resulting N‐Boc‐1‐[2‐(carbomethoxy)aryl]furfurylamines was demonstrated by their facile two‐step transformation into 2‐methyl‐6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are employed in high‐performance cyclometalated OLEDs.
Straightforward functionalization of furans by means of a three‐component Mannich‐type condensation reaction with methyl 2‐formylbenzoates and carbamates was accomplished. The synthetic utility of the resultant N‐Boc arylfurfurylamines was demonstrated by a practical two‐step strategy that leads to 6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are used as cyclometalating ligands for OLEDs. |
| doi_str_mv | 10.1002/ejoc.201701355 |
| format | Article |
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Straightforward functionalization of furans by means of a three‐component Mannich‐type condensation reaction with methyl 2‐formylbenzoates and carbamates was accomplished. The synthetic utility of the resultant N‐Boc arylfurfurylamines was demonstrated by a practical two‐step strategy that leads to 6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are used as cyclometalating ligands for OLEDs.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201701355</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>6H‐Isochromeno[4,3‐b]pyridine‐6‐ones ; Aromatic compounds ; Carbamates (tradename) ; Esters ; Furans ; Fused‐ring systems ; Iodine ; Iodine‐mediated reactions ; Multicomponent reactions ; Organic light emitting diodes ; Ring opening ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2018-01, Vol.2018 (4), p.461-469</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-3208-2568 ; 0000-0003-3009-7221</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201701355$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201701355$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Shpuntov, Pavel M.</creatorcontrib><creatorcontrib>Kolodina, Alexandra A.</creatorcontrib><creatorcontrib>Uchuskin, Maxim G.</creatorcontrib><creatorcontrib>Abaev, Vladimir T.</creatorcontrib><title>Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters</title><title>European journal of organic chemistry</title><description>An efficient iodine‐catalyzed three‐component Mannich‐type reaction of various 2‐alkylfurans, methyl 2‐formylbenzoates and carbamates under mild reaction conditions was realized. Synthetic utility of the resulting N‐Boc‐1‐[2‐(carbomethoxy)aryl]furfurylamines was demonstrated by their facile two‐step transformation into 2‐methyl‐6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are employed in high‐performance cyclometalated OLEDs.
Straightforward functionalization of furans by means of a three‐component Mannich‐type condensation reaction with methyl 2‐formylbenzoates and carbamates was accomplished. The synthetic utility of the resultant N‐Boc arylfurfurylamines was demonstrated by a practical two‐step strategy that leads to 6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are used as cyclometalating ligands for OLEDs.</description><subject>6H‐Isochromeno[4,3‐b]pyridine‐6‐ones</subject><subject>Aromatic compounds</subject><subject>Carbamates (tradename)</subject><subject>Esters</subject><subject>Furans</subject><subject>Fused‐ring systems</subject><subject>Iodine</subject><subject>Iodine‐mediated reactions</subject><subject>Multicomponent reactions</subject><subject>Organic light emitting diodes</subject><subject>Ring opening</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNo9UV1LHDEUHUqFWvW1z4G-dmxuMolJ34Zl_SjKiigURIZMku1kick0ma3Mmz-h4N_x1_hLOuuKD5dzPw7n3sspii-ADwFj8t2uoj4kGI4wUMY-FLuApSwxl_jjlFe0KkHSX5-KzzmvMMaSc9gtno_XSQV05cJvtOht2ODL4xO6HJMzLtjtZOZjXif7A9UBzZdLp50NA6r7PkWlOzTEB5VMRvz05fHfWY66S_HehnhbfaNTp73rt2pTzqeIwWa0nCjoyirj_Ijqv8p51XqLXs_JSAWDLruhU155Y7vROI1q7Qy6sEM3ejTPg015v9hZKp_twRvuFTfH8-vZaXm-ODmb1eflikjJSkpaqRUF3mLQRBPBKxAVM1QB1kCVYBwTw0QlKg0gjoxQHDS0spWSC9bSveLrVnf698_a5qFZxXUK08oGpCRMAmFiYskt68F5OzZ9cvcqjQ3gZmNPs7Gnebenmf9czN4r-h_07IwY</recordid><startdate>20180131</startdate><enddate>20180131</enddate><creator>Shpuntov, Pavel M.</creator><creator>Kolodina, Alexandra A.</creator><creator>Uchuskin, Maxim G.</creator><creator>Abaev, Vladimir T.</creator><general>Wiley Subscription Services, Inc</general><scope/><orcidid>https://orcid.org/0000-0003-3208-2568</orcidid><orcidid>https://orcid.org/0000-0003-3009-7221</orcidid></search><sort><creationdate>20180131</creationdate><title>Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters</title><author>Shpuntov, Pavel M. ; Kolodina, Alexandra A. ; Uchuskin, Maxim G. ; Abaev, Vladimir T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j2995-32b9ca316b01c2c28641845d3a10c13a85602d58484c1187d8a61c1b9b99685b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>6H‐Isochromeno[4,3‐b]pyridine‐6‐ones</topic><topic>Aromatic compounds</topic><topic>Carbamates (tradename)</topic><topic>Esters</topic><topic>Furans</topic><topic>Fused‐ring systems</topic><topic>Iodine</topic><topic>Iodine‐mediated reactions</topic><topic>Multicomponent reactions</topic><topic>Organic light emitting diodes</topic><topic>Ring opening</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shpuntov, Pavel M.</creatorcontrib><creatorcontrib>Kolodina, Alexandra A.</creatorcontrib><creatorcontrib>Uchuskin, Maxim G.</creatorcontrib><creatorcontrib>Abaev, Vladimir T.</creatorcontrib><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shpuntov, Pavel M.</au><au>Kolodina, Alexandra A.</au><au>Uchuskin, Maxim G.</au><au>Abaev, Vladimir T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-01-31</date><risdate>2018</risdate><volume>2018</volume><issue>4</issue><spage>461</spage><epage>469</epage><pages>461-469</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient iodine‐catalyzed three‐component Mannich‐type reaction of various 2‐alkylfurans, methyl 2‐formylbenzoates and carbamates under mild reaction conditions was realized. Synthetic utility of the resulting N‐Boc‐1‐[2‐(carbomethoxy)aryl]furfurylamines was demonstrated by their facile two‐step transformation into 2‐methyl‐6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are employed in high‐performance cyclometalated OLEDs.
Straightforward functionalization of furans by means of a three‐component Mannich‐type condensation reaction with methyl 2‐formylbenzoates and carbamates was accomplished. The synthetic utility of the resultant N‐Boc arylfurfurylamines was demonstrated by a practical two‐step strategy that leads to 6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are used as cyclometalating ligands for OLEDs.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201701355</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-3208-2568</orcidid><orcidid>https://orcid.org/0000-0003-3009-7221</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2018-01, Vol.2018 (4), p.461-469 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| subjects | 6H‐Isochromeno[4,3‐b]pyridine‐6‐ones Aromatic compounds Carbamates (tradename) Esters Furans Fused‐ring systems Iodine Iodine‐mediated reactions Multicomponent reactions Organic light emitting diodes Ring opening Synthetic methods |
| title | Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters |
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