Practical Synthesis of Chromeno[2,3‐b]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy
The synthesis of chromeno[2,3‐b]indole from simple starting materials remains a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Mor...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2017-02, Vol.12 (4), p.401-404 |
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| container_title | Chemistry, an Asian journal |
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| creator | Liu, Jianming Liu, Na Yue, Yuanyuan Wang, Yanyan Chen, Kaige Zhang, Jia Zhao, Shufang Zhuo, Kelei |
| description | The synthesis of chromeno[2,3‐b]indole from simple starting materials remains a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis of the product could be achieved under the optimized condition.
One, [2,3‐b]indoles: The synthesis of chromeno[2,3‐b]indoles from simple starting materials is a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis was possible. |
| doi_str_mv | 10.1002/asia.201601681 |
| format | Article |
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One, [2,3‐b]indoles: The synthesis of chromeno[2,3‐b]indoles from simple starting materials is a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis was possible.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201601681</identifier><identifier>PMID: 28111933</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>aldehydes ; Chemistry ; cyclization ; heterocycles ; indoles ; palladium</subject><ispartof>Chemistry, an Asian journal, 2017-02, Vol.12 (4), p.401-404</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4761-70f49cc3dde26c63dad8ec6cd9f1289f608630c6e2e257482923551cb923f7543</citedby><cites>FETCH-LOGICAL-c4761-70f49cc3dde26c63dad8ec6cd9f1289f608630c6e2e257482923551cb923f7543</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.201601681$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201601681$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28111933$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Jianming</creatorcontrib><creatorcontrib>Liu, Na</creatorcontrib><creatorcontrib>Yue, Yuanyuan</creatorcontrib><creatorcontrib>Wang, Yanyan</creatorcontrib><creatorcontrib>Chen, Kaige</creatorcontrib><creatorcontrib>Zhang, Jia</creatorcontrib><creatorcontrib>Zhao, Shufang</creatorcontrib><creatorcontrib>Zhuo, Kelei</creatorcontrib><title>Practical Synthesis of Chromeno[2,3‐b]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy</title><title>Chemistry, an Asian journal</title><addtitle>Chem Asian J</addtitle><description>The synthesis of chromeno[2,3‐b]indole from simple starting materials remains a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis of the product could be achieved under the optimized condition.
One, [2,3‐b]indoles: The synthesis of chromeno[2,3‐b]indoles from simple starting materials is a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis was possible.</description><subject>aldehydes</subject><subject>Chemistry</subject><subject>cyclization</subject><subject>heterocycles</subject><subject>indoles</subject><subject>palladium</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkc9q3DAQh0VoyL_mmmMR9JJDdleSLVs6mqVJFxYS2AQKpRitNM4q9UpbyU5wT32EPmOeJDabbKCXgmA08M3HMD-EzigZU0LYREWrxozQrH-C7qEjKjI6SnP67cPuz8QhOo7xgRDOiBQH6JAJSqlMkiPkboLSjdWqxovONSuINmJf4ekq-DU4_51dJM9__i5_WGd8DXjxE2povMOPVmHlcFEbWHUG8FXw7QbPXITQWO8mRT-vGvtbDR1eNEE1cN99RPuVqiOcvtYTdHf55Xb6dTS_vppNi_lIp3m_c06qVGqdGAMs01lilBGgM21kRZmQVUZElhCdAQPG81QwyRLOqV72tcp5mpyg8613E_yvFmJTrm3UUNfKgW9jOVyGSyY479HP_6APvg2u326gBGecy0E43lI6-BgDVOUm2LUKXUlJOSRRDkmUuyT6gU-v2na5BrPD307fA3ILPNkauv_oymIxK97lLwNQlg0</recordid><startdate>20170216</startdate><enddate>20170216</enddate><creator>Liu, Jianming</creator><creator>Liu, Na</creator><creator>Yue, Yuanyuan</creator><creator>Wang, Yanyan</creator><creator>Chen, Kaige</creator><creator>Zhang, Jia</creator><creator>Zhao, Shufang</creator><creator>Zhuo, Kelei</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20170216</creationdate><title>Practical Synthesis of Chromeno[2,3‐b]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy</title><author>Liu, Jianming ; Liu, Na ; Yue, Yuanyuan ; Wang, Yanyan ; Chen, Kaige ; Zhang, Jia ; Zhao, Shufang ; Zhuo, Kelei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4761-70f49cc3dde26c63dad8ec6cd9f1289f608630c6e2e257482923551cb923f7543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>aldehydes</topic><topic>Chemistry</topic><topic>cyclization</topic><topic>heterocycles</topic><topic>indoles</topic><topic>palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Jianming</creatorcontrib><creatorcontrib>Liu, Na</creatorcontrib><creatorcontrib>Yue, Yuanyuan</creatorcontrib><creatorcontrib>Wang, Yanyan</creatorcontrib><creatorcontrib>Chen, Kaige</creatorcontrib><creatorcontrib>Zhang, Jia</creatorcontrib><creatorcontrib>Zhao, Shufang</creatorcontrib><creatorcontrib>Zhuo, Kelei</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Jianming</au><au>Liu, Na</au><au>Yue, Yuanyuan</au><au>Wang, Yanyan</au><au>Chen, Kaige</au><au>Zhang, Jia</au><au>Zhao, Shufang</au><au>Zhuo, Kelei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Practical Synthesis of Chromeno[2,3‐b]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem Asian J</addtitle><date>2017-02-16</date><risdate>2017</risdate><volume>12</volume><issue>4</issue><spage>401</spage><epage>404</epage><pages>401-404</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>The synthesis of chromeno[2,3‐b]indole from simple starting materials remains a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis of the product could be achieved under the optimized condition.
One, [2,3‐b]indoles: The synthesis of chromeno[2,3‐b]indoles from simple starting materials is a demanding process. Herein, 2‐bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3‐b]indoles. Moreover, various functional groups were tolerated and a gram‐scale synthesis was possible.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28111933</pmid><doi>10.1002/asia.201601681</doi><tpages>4</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | aldehydes Chemistry cyclization heterocycles indoles palladium |
| title | Practical Synthesis of Chromeno[2,3‐b]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy |
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