Iron-Catalyzed Intramolecular C(sp 2)–N Cyclization of 1‑(N‑Arylpyrrol-2-yl)ethanone O‑Acetyl Oximes toward Pyrrolo[1,2‑a]quinoxaline Derivatives
An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N–O bond cleavage and intramolecular directed C–H arylation reactions in acetic acid.
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2015-07, Vol.80 (13), p.6875-6884 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 6884 |
---|---|
container_issue | 13 |
container_start_page | 6875 |
container_title | Journal of organic chemistry |
container_volume | 80 |
creator | Zhang, Zhiguo Li, Junlong Zhang, Guisheng Ma, Nana Liu, Qingfeng Liu, Tongxin |
description | An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N–O bond cleavage and intramolecular directed C–H arylation reactions in acetic acid. |
doi_str_mv | 10.1021/acs.joc.5b00915 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1693725464</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1693725464</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-3fe8dca59f5fe2668aa4e6ba10bf2e321e0df0ccfc9e63ead0c9f82e860cac4e3</originalsourceid><addsrcrecordid>eNp1kbtu2zAUhomiQeOknbsVHB2kcngRaWsM1EsMBHGHdioK4Zg6RBVQokNKSZQpr1B07NvlScLEbrdyOBzO9_8E8RHylrMZZ4KfgImzS29mas1YwdULMuFKsEwXLH9JJowJkUmh5T45iPGSpaOUekX2hWZqPpfzCfmzDL7LSujBjXdY02XXB2i9QzM4CLScxg0VRw_3vy9oORrX3EHf-I56S_nD_a_pRRqnYXSbMQTvMpGN7gj7n9D5DunqaWmwHx1d3TYtRtr7Gwg1_fJM--_8vUgI_Lgams7fgmtS6AOG5jo9co3xNdmz4CK-2d2H5Nunj1_Ls-x89XlZnp5nIIuiz6TFRW1AFVZZFFovAHLUa-BsbQVKwZHVlhljTYFaItTMFHYhcKGZAZOjPCTTbe8m-KsBY1-1TTToHHToh1hxXci5ULnOE3qyRU3wMQa01SY0LYSx4qx6MlIlI1UyUu2MpMS7XfmwbrH-x_9VkIDjLbBNDqFLf_1v3SMjsZ6_</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1693725464</pqid></control><display><type>article</type><title>Iron-Catalyzed Intramolecular C(sp 2)–N Cyclization of 1‑(N‑Arylpyrrol-2-yl)ethanone O‑Acetyl Oximes toward Pyrrolo[1,2‑a]quinoxaline Derivatives</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Zhang, Zhiguo ; Li, Junlong ; Zhang, Guisheng ; Ma, Nana ; Liu, Qingfeng ; Liu, Tongxin</creator><creatorcontrib>Zhang, Zhiguo ; Li, Junlong ; Zhang, Guisheng ; Ma, Nana ; Liu, Qingfeng ; Liu, Tongxin</creatorcontrib><description>An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N–O bond cleavage and intramolecular directed C–H arylation reactions in acetic acid.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b00915</identifier><identifier>PMID: 26057737</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Cyclization ; Iron - chemistry ; Molecular Structure ; Oximes - chemistry ; Pyrroles - chemical synthesis ; Pyrroles - chemistry ; Quinoxalines - chemistry</subject><ispartof>Journal of organic chemistry, 2015-07, Vol.80 (13), p.6875-6884</ispartof><rights>Copyright © American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-3fe8dca59f5fe2668aa4e6ba10bf2e321e0df0ccfc9e63ead0c9f82e860cac4e3</citedby><cites>FETCH-LOGICAL-a399t-3fe8dca59f5fe2668aa4e6ba10bf2e321e0df0ccfc9e63ead0c9f82e860cac4e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.5b00915$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.5b00915$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26057737$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Zhiguo</creatorcontrib><creatorcontrib>Li, Junlong</creatorcontrib><creatorcontrib>Zhang, Guisheng</creatorcontrib><creatorcontrib>Ma, Nana</creatorcontrib><creatorcontrib>Liu, Qingfeng</creatorcontrib><creatorcontrib>Liu, Tongxin</creatorcontrib><title>Iron-Catalyzed Intramolecular C(sp 2)–N Cyclization of 1‑(N‑Arylpyrrol-2-yl)ethanone O‑Acetyl Oximes toward Pyrrolo[1,2‑a]quinoxaline Derivatives</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N–O bond cleavage and intramolecular directed C–H arylation reactions in acetic acid.</description><subject>Catalysis</subject><subject>Cyclization</subject><subject>Iron - chemistry</subject><subject>Molecular Structure</subject><subject>Oximes - chemistry</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Quinoxalines - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kbtu2zAUhomiQeOknbsVHB2kcngRaWsM1EsMBHGHdioK4Zg6RBVQokNKSZQpr1B07NvlScLEbrdyOBzO9_8E8RHylrMZZ4KfgImzS29mas1YwdULMuFKsEwXLH9JJowJkUmh5T45iPGSpaOUekX2hWZqPpfzCfmzDL7LSujBjXdY02XXB2i9QzM4CLScxg0VRw_3vy9oORrX3EHf-I56S_nD_a_pRRqnYXSbMQTvMpGN7gj7n9D5DunqaWmwHx1d3TYtRtr7Gwg1_fJM--_8vUgI_Lgams7fgmtS6AOG5jo9co3xNdmz4CK-2d2H5Nunj1_Ls-x89XlZnp5nIIuiz6TFRW1AFVZZFFovAHLUa-BsbQVKwZHVlhljTYFaItTMFHYhcKGZAZOjPCTTbe8m-KsBY1-1TTToHHToh1hxXci5ULnOE3qyRU3wMQa01SY0LYSx4qx6MlIlI1UyUu2MpMS7XfmwbrH-x_9VkIDjLbBNDqFLf_1v3SMjsZ6_</recordid><startdate>20150702</startdate><enddate>20150702</enddate><creator>Zhang, Zhiguo</creator><creator>Li, Junlong</creator><creator>Zhang, Guisheng</creator><creator>Ma, Nana</creator><creator>Liu, Qingfeng</creator><creator>Liu, Tongxin</creator><general>American Chemical Society</general><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>20150702</creationdate><title>Iron-Catalyzed Intramolecular C(sp 2)–N Cyclization of 1‑(N‑Arylpyrrol-2-yl)ethanone O‑Acetyl Oximes toward Pyrrolo[1,2‑a]quinoxaline Derivatives</title><author>Zhang, Zhiguo ; Li, Junlong ; Zhang, Guisheng ; Ma, Nana ; Liu, Qingfeng ; Liu, Tongxin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-3fe8dca59f5fe2668aa4e6ba10bf2e321e0df0ccfc9e63ead0c9f82e860cac4e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Catalysis</topic><topic>Cyclization</topic><topic>Iron - chemistry</topic><topic>Molecular Structure</topic><topic>Oximes - chemistry</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Quinoxalines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhiguo</creatorcontrib><creatorcontrib>Li, Junlong</creatorcontrib><creatorcontrib>Zhang, Guisheng</creatorcontrib><creatorcontrib>Ma, Nana</creatorcontrib><creatorcontrib>Liu, Qingfeng</creatorcontrib><creatorcontrib>Liu, Tongxin</creatorcontrib><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>Zhang, Zhiguo</au><au>Li, Junlong</au><au>Zhang, Guisheng</au><au>Ma, Nana</au><au>Liu, Qingfeng</au><au>Liu, Tongxin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iron-Catalyzed Intramolecular C(sp 2)–N Cyclization of 1‑(N‑Arylpyrrol-2-yl)ethanone O‑Acetyl Oximes toward Pyrrolo[1,2‑a]quinoxaline Derivatives</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-07-02</date><risdate>2015</risdate><volume>80</volume><issue>13</issue><spage>6875</spage><epage>6884</epage><pages>6875-6884</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An efficient and convenient iron-catalyzed protocol has been developed for the synthesis of substituted pyrrolo[1,2-a]quinoxalines from 1-(N-arylpyrrol-2-yl)ethanone O-acetyl oximes through N–O bond cleavage and intramolecular directed C–H arylation reactions in acetic acid.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26057737</pmid><doi>10.1021/acs.joc.5b00915</doi><tpages>10</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0022-3263 |
ispartof | Journal of organic chemistry, 2015-07, Vol.80 (13), p.6875-6884 |
issn | 0022-3263 1520-6904 |
language | eng |
recordid | cdi_proquest_miscellaneous_1693725464 |
source | MEDLINE; American Chemical Society Journals |
subjects | Catalysis Cyclization Iron - chemistry Molecular Structure Oximes - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Quinoxalines - chemistry |
title | Iron-Catalyzed Intramolecular C(sp 2)–N Cyclization of 1‑(N‑Arylpyrrol-2-yl)ethanone O‑Acetyl Oximes toward Pyrrolo[1,2‑a]quinoxaline Derivatives |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T10%3A00%3A55IST&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=Iron-Catalyzed%20Intramolecular%20C(sp%202)%E2%80%93N%20Cyclization%20of%201%E2%80%91(N%E2%80%91Arylpyrrol-2-yl)ethanone%20O%E2%80%91Acetyl%20Oximes%20toward%20Pyrrolo%5B1,2%E2%80%91a%5Dquinoxaline%20Derivatives&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Zhang,%20Zhiguo&rft.date=2015-07-02&rft.volume=80&rft.issue=13&rft.spage=6875&rft.epage=6884&rft.pages=6875-6884&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.5b00915&rft_dat=%3Cproquest_cross%3E1693725464%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1693725464&rft_id=info:pmid/26057737&rfr_iscdi=true |