Loading…
Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes
In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazol...
Saved in:
| Published in: | Journal of organic chemistry 2010-02, Vol.75 (3), p.992-994 |
|---|---|
| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33 |
|---|---|
| cites | cdi_FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33 |
| container_end_page | 994 |
| container_issue | 3 |
| container_start_page | 992 |
| container_title | Journal of organic chemistry |
| container_volume | 75 |
| creator | Reeves, Jonathan T Fandrick, Daniel R Tan, Zhulin Song, Jinhua J Lee, Heewon Yee, Nathan K Senanayake, Chris H |
| description | In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole. |
| doi_str_mv | 10.1021/jo9025644 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_733851117</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>733851117</sourcerecordid><originalsourceid>FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33</originalsourceid><addsrcrecordid>eNpt0M9LwzAUB_AgipvTg_-A9CLiofryo81yHNWpMPCi5_LWJtjRJjVpke2vt2Nzuxh45PLh-x5fQq4pPFBg9HHlFLAkFeKEjGnCIE4ViFMyBmAs5izlI3IRwgqGlyTJORkxACGZkmPylLm21T7OsMN6vdFlNLO2r7GrnI2ciVg8d75Z17hxtQ7RT9V9RS6eNZV1lSsdem11uCRnBuugr_b_hHzOnz-y13jx_vKWzRYxciG6mEpUuGRGo1SqmCaMG5MaDkYAg4IrKJlhFHE4vixTtpQSBUyl2g4OgE_I3S639e6716HLmyoUuq7RateHXHI-TSilcpD3O1l4F4LXJm991aBf5xTybWf5obPB3uxT-2Wjy4P8K2kAt3uAocDaeLRFFY6OCQA-5UeHRRjye2-HMv5Z-AsalX35</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>733851117</pqid></control><display><type>article</type><title>Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Reeves, Jonathan T ; Fandrick, Daniel R ; Tan, Zhulin ; Song, Jinhua J ; Lee, Heewon ; Yee, Nathan K ; Senanayake, Chris H</creator><creatorcontrib>Reeves, Jonathan T ; Fandrick, Daniel R ; Tan, Zhulin ; Song, Jinhua J ; Lee, Heewon ; Yee, Nathan K ; Senanayake, Chris H</creatorcontrib><description>In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo9025644</identifier><identifier>PMID: 20047297</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Azoles - chemical synthesis ; Azoles - chemistry ; Catalysis ; Chemistry ; Copper - chemistry ; Cross-Linking Reagents ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Molecular Structure ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2010-02, Vol.75 (3), p.992-994</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33</citedby><cites>FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22400383$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20047297$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Reeves, Jonathan T</creatorcontrib><creatorcontrib>Fandrick, Daniel R</creatorcontrib><creatorcontrib>Tan, Zhulin</creatorcontrib><creatorcontrib>Song, Jinhua J</creatorcontrib><creatorcontrib>Lee, Heewon</creatorcontrib><creatorcontrib>Yee, Nathan K</creatorcontrib><creatorcontrib>Senanayake, Chris H</creatorcontrib><title>Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.</description><subject>Azoles - chemical synthesis</subject><subject>Azoles - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Copper - chemistry</subject><subject>Cross-Linking Reagents</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNpt0M9LwzAUB_AgipvTg_-A9CLiofryo81yHNWpMPCi5_LWJtjRJjVpke2vt2Nzuxh45PLh-x5fQq4pPFBg9HHlFLAkFeKEjGnCIE4ViFMyBmAs5izlI3IRwgqGlyTJORkxACGZkmPylLm21T7OsMN6vdFlNLO2r7GrnI2ciVg8d75Z17hxtQ7RT9V9RS6eNZV1lSsdem11uCRnBuugr_b_hHzOnz-y13jx_vKWzRYxciG6mEpUuGRGo1SqmCaMG5MaDkYAg4IrKJlhFHE4vixTtpQSBUyl2g4OgE_I3S639e6716HLmyoUuq7RateHXHI-TSilcpD3O1l4F4LXJm991aBf5xTybWf5obPB3uxT-2Wjy4P8K2kAt3uAocDaeLRFFY6OCQA-5UeHRRjye2-HMv5Z-AsalX35</recordid><startdate>20100205</startdate><enddate>20100205</enddate><creator>Reeves, Jonathan T</creator><creator>Fandrick, Daniel R</creator><creator>Tan, Zhulin</creator><creator>Song, Jinhua J</creator><creator>Lee, Heewon</creator><creator>Yee, Nathan K</creator><creator>Senanayake, Chris H</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100205</creationdate><title>Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes</title><author>Reeves, Jonathan T ; Fandrick, Daniel R ; Tan, Zhulin ; Song, Jinhua J ; Lee, Heewon ; Yee, Nathan K ; Senanayake, Chris H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Azoles - chemical synthesis</topic><topic>Azoles - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Copper - chemistry</topic><topic>Cross-Linking Reagents</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reeves, Jonathan T</creatorcontrib><creatorcontrib>Fandrick, Daniel R</creatorcontrib><creatorcontrib>Tan, Zhulin</creatorcontrib><creatorcontrib>Song, Jinhua J</creatorcontrib><creatorcontrib>Lee, Heewon</creatorcontrib><creatorcontrib>Yee, Nathan K</creatorcontrib><creatorcontrib>Senanayake, Chris H</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reeves, Jonathan T</au><au>Fandrick, Daniel R</au><au>Tan, Zhulin</au><au>Song, Jinhua J</au><au>Lee, Heewon</au><au>Yee, Nathan K</au><au>Senanayake, Chris H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-02-05</date><risdate>2010</risdate><volume>75</volume><issue>3</issue><spage>992</spage><epage>994</epage><pages>992-994</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>In the presence of catalytic CuI and sparteine, 2-formylpyrroles can be annulated with o-aminoiodoarenes to give substituted pyrrolo[1,2-a]quinoxalines and related heterocycles. The reaction also works for annulation of 2-formylindoles, 2-formylimidazole, 2-formylbenzimidazole, and a 3-formylpyrazole.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20047297</pmid><doi>10.1021/jo9025644</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2010-02, Vol.75 (3), p.992-994 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_733851117 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Azoles - chemical synthesis Azoles - chemistry Catalysis Chemistry Copper - chemistry Cross-Linking Reagents Exact sciences and technology Heterocyclic compounds Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Molecular Structure Organic chemistry Preparations and properties |
| title | Copper-Catalyzed Annulation of 2-Formylazoles with o-Aminoiodoarenes |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T23%3A07%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper-Catalyzed%20Annulation%20of%202-Formylazoles%20with%20o-Aminoiodoarenes&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Reeves,%20Jonathan%20T&rft.date=2010-02-05&rft.volume=75&rft.issue=3&rft.spage=992&rft.epage=994&rft.pages=992-994&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo9025644&rft_dat=%3Cproquest_cross%3E733851117%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a344t-17a9ab2fea799c8523ff6f30f4020c390d2f21aa904dd62b77a408790879a0c33%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=733851117&rft_id=info:pmid/20047297&rfr_iscdi=true |