Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C­(sp3)–H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4­...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2015-11, Vol.80 (22), p.11351-11359
Hauptverfasser: Laha, Joydev K, Tummalapalli, K. S. Satyanarayana, Nair, Akshay, Patel, Nidhi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 11359
container_issue 22
container_start_page 11351
container_title Journal of organic chemistry
container_volume 80
creator Laha, Joydev K
Tummalapalli, K. S. Satyanarayana
Nair, Akshay
Patel, Nidhi
description A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C­(sp3)–H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4­(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.
doi_str_mv 10.1021/acs.joc.5b01872
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1735336778</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1735336778</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-a3350a13f4e3d7bc2b1496ff89f7d6b6c46d3f0fa4d42adaf62f112a2edf5f23</originalsourceid><addsrcrecordid>eNp1kc1uEzEUhS0EomlhzQ55mQol8c_Yk1mGqJBKbSOR7kce_4CrGXuwZ6ROV3kF1DfgHXihPAkuk3aHF_f4Wt85knUA-IDRHCOCF0LG-Z2Xc1YhvMzJKzDBjKAZL1D2GkwQImRGCacn4DTGO5QOY-wtOCGckQwt6QT82fW1EZ2G34SyUtRw5ax3cLrbZvCw_33YP57Da61sQhRcT2NLz9PbBt7YLvjv2oku4Yvt_fB8h9bBm8P-1yoMNfys3cNQWwlXjXU6wov7VjiVkrofGu6kbzU0Pozb4JJEG6E3_3yisSqZUrZ4SAo3utPBy0HWOr4Db4yoo35_1DNw--Xidr2ZXW2_Xq5XVzNBi6JLkzIkMDWZpiqvJKlwVnBjloXJFa-4zLiiBhmRqYwIJQwnBmMiiFaGGULPwHSMbYP_2evYlY2NUte1cNr3scQ5ZZTyPF8mdDGiMvgYgzZlG2wjwlBiVD5VVaaqylRVeawqOT4ew_uq0eqFf-4mAZ9GYHT2waWv_jfuL3f-pSY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1735336778</pqid></control><display><type>article</type><title>Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles</title><source>ACS Publications</source><creator>Laha, Joydev K ; Tummalapalli, K. S. Satyanarayana ; Nair, Akshay ; Patel, Nidhi</creator><creatorcontrib>Laha, Joydev K ; Tummalapalli, K. S. Satyanarayana ; Nair, Akshay ; Patel, Nidhi</creatorcontrib><description>A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C­(sp3)–H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4­(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b01872</identifier><identifier>PMID: 26524083</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2015-11, Vol.80 (22), p.11351-11359</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-a3350a13f4e3d7bc2b1496ff89f7d6b6c46d3f0fa4d42adaf62f112a2edf5f23</citedby><cites>FETCH-LOGICAL-a399t-a3350a13f4e3d7bc2b1496ff89f7d6b6c46d3f0fa4d42adaf62f112a2edf5f23</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.5b01872$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.5b01872$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26524083$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Laha, Joydev K</creatorcontrib><creatorcontrib>Tummalapalli, K. S. Satyanarayana</creatorcontrib><creatorcontrib>Nair, Akshay</creatorcontrib><creatorcontrib>Patel, Nidhi</creatorcontrib><title>Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C­(sp3)–H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4­(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp1kc1uEzEUhS0EomlhzQ55mQol8c_Yk1mGqJBKbSOR7kce_4CrGXuwZ6ROV3kF1DfgHXihPAkuk3aHF_f4Wt85knUA-IDRHCOCF0LG-Z2Xc1YhvMzJKzDBjKAZL1D2GkwQImRGCacn4DTGO5QOY-wtOCGckQwt6QT82fW1EZ2G34SyUtRw5ax3cLrbZvCw_33YP57Da61sQhRcT2NLz9PbBt7YLvjv2oku4Yvt_fB8h9bBm8P-1yoMNfys3cNQWwlXjXU6wov7VjiVkrofGu6kbzU0Pozb4JJEG6E3_3yisSqZUrZ4SAo3utPBy0HWOr4Db4yoo35_1DNw--Xidr2ZXW2_Xq5XVzNBi6JLkzIkMDWZpiqvJKlwVnBjloXJFa-4zLiiBhmRqYwIJQwnBmMiiFaGGULPwHSMbYP_2evYlY2NUte1cNr3scQ5ZZTyPF8mdDGiMvgYgzZlG2wjwlBiVD5VVaaqylRVeawqOT4ew_uq0eqFf-4mAZ9GYHT2waWv_jfuL3f-pSY</recordid><startdate>20151120</startdate><enddate>20151120</enddate><creator>Laha, Joydev K</creator><creator>Tummalapalli, K. S. Satyanarayana</creator><creator>Nair, Akshay</creator><creator>Patel, Nidhi</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20151120</creationdate><title>Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles</title><author>Laha, Joydev K ; Tummalapalli, K. S. Satyanarayana ; Nair, Akshay ; Patel, Nidhi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-a3350a13f4e3d7bc2b1496ff89f7d6b6c46d3f0fa4d42adaf62f112a2edf5f23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Laha, Joydev K</creatorcontrib><creatorcontrib>Tummalapalli, K. S. Satyanarayana</creatorcontrib><creatorcontrib>Nair, Akshay</creatorcontrib><creatorcontrib>Patel, Nidhi</creatorcontrib><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>Laha, Joydev K</au><au>Tummalapalli, K. S. Satyanarayana</au><au>Nair, Akshay</au><au>Patel, Nidhi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-11-20</date><risdate>2015</risdate><volume>80</volume><issue>22</issue><spage>11351</spage><epage>11359</epage><pages>11351-11359</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A transition-metal-free, K2S2O8-mediated intramolecular oxidative nitrogenation/oxygenation of C­(sp3)–H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4­(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26524083</pmid><doi>10.1021/acs.joc.5b01872</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2015-11, Vol.80 (22), p.11351-11359
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1735336778
source ACS Publications
title Sulfate Radical Anion (SO4 •–) Mediated C(sp3)–H Nitrogenation/Oxygenation in N‑Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T07%3A16%3A46IST&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=Sulfate%20Radical%20Anion%20(SO4%20%E2%80%A2%E2%80%93)%20Mediated%20C(sp3)%E2%80%93H%20Nitrogenation/Oxygenation%20in%20N%E2%80%91Aryl%20Benzylic%20Amines%20Expanded%20the%20Scope%20for%20the%20Synthesis%20of%20Benzamidine/Oxazine%20Heterocycles&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Laha,%20Joydev%20K&rft.date=2015-11-20&rft.volume=80&rft.issue=22&rft.spage=11351&rft.epage=11359&rft.pages=11351-11359&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.5b01872&rft_dat=%3Cproquest_cross%3E1735336778%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=1735336778&rft_id=info:pmid/26524083&rfr_iscdi=true