Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids

The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation an...

Full description

Saved in:
Bibliographic Details
Published in:Beilstein journal of organic chemistry 2016-05, Vol.12 (1), p.874-881
Main Authors: Dzhons, Daria Yu, Budruev, Andrei V
Format: Article
Language:English
Subjects:
1,5-electrocyclization
2,1-benzisoxazolones
aryl azides
azepinones
Chemistry
Full Research Paper
nitrenes
photochemical cyclization
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-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53
cites cdi_FETCH-LOGICAL-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53
container_end_page 881
container_issue 1
container_start_page 874
container_title Beilstein journal of organic chemistry
container_volume 12
creator Dzhons, Daria Yu
Budruev, Andrei V
description The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.
doi_str_mv 10.3762/bjoc.12.86
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_450e8978d86d42678510e4510618f2bf</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_450e8978d86d42678510e4510618f2bf</doaj_id><sourcerecordid>1799558608</sourcerecordid><originalsourceid>FETCH-LOGICAL-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53</originalsourceid><addsrcrecordid>eNpdkttrFDEUhwdR7EVf_ANkwJdWzJr75UWQorZQ7IP6HHI5s5tldrJOZsVd8H83262l9SUJJx8fh3N-TfOK4BlTkr73yxxmhM60fNIcEy0xEsyopw_eR81JKUuMOZZYPm-OqGIcc6WPmz_ftsO0gJJKm7uWviPIw7BLJf92u9wDYmfk8hzlAUrrt613BdAKYnITxHa9yFMOC1il4Pr2K7ppfR4i6vK4SsO8DdvQp52bUh5u3cjtUsx7fU6hdSHF8qJ51rm-wMu7-7T58fnT94tLdH3z5eri4zUKXNEJATgsO-076RRX0YdgDPE-6k4rDcZ5JZUWTPFaE0JGZQSJRDEqOzDECXbaXB28MbulXY9p5catzS7Z20Ie59aNUwo9WC4waKN01DJyuvcSDLwekuiO-q66Phxc642vowgwTKPrH0kf_wxpYef5l-UGUyx4FZzdCcb8cwNlsqtUAvS9GyBviiXKGCHq6nRF3_yHLvNmHOqoLDGCcUoYVpV6e6DCmEsZobtvhmC7T4jdJ8QSarWs8OuH7d-j_yLB_gKvAbcg</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1953421307</pqid></control><display><type>article</type><title>Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids</title><source>Publicly Available Content Database</source><source>PubMed Central</source><creator>Dzhons, Daria Yu ; Budruev, Andrei V</creator><creatorcontrib>Dzhons, Daria Yu ; Budruev, Andrei V</creatorcontrib><description>The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.</description><identifier>ISSN: 1860-5397</identifier><identifier>ISSN: 2195-951X</identifier><identifier>EISSN: 1860-5397</identifier><identifier>DOI: 10.3762/bjoc.12.86</identifier><identifier>PMID: 27340478</identifier><language>eng</language><publisher>Germany: Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</publisher><subject>1,5-electrocyclization ; 2,1-benzisoxazolones ; aryl azides ; azepinones ; Chemistry ; Full Research Paper ; nitrenes ; photochemical cyclization</subject><ispartof>Beilstein journal of organic chemistry, 2016-05, Vol.12 (1), p.874-881</ispartof><rights>Copyright © 2016, Dzhons and Budruev; licensee Beilstein-Institut. This work is licensed under the Creative Commons Attribution License (https://creativecommons.org/licenses/by/3.0/) (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Copyright © 2016, Dzhons and Budruev 2016 Dzhons and Budruev</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53</citedby><cites>FETCH-LOGICAL-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1953421307/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1953421307?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27340478$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dzhons, Daria Yu</creatorcontrib><creatorcontrib>Budruev, Andrei V</creatorcontrib><title>Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids</title><title>Beilstein journal of organic chemistry</title><addtitle>Beilstein J Org Chem</addtitle><description>The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.</description><subject>1,5-electrocyclization</subject><subject>2,1-benzisoxazolones</subject><subject>aryl azides</subject><subject>azepinones</subject><subject>Chemistry</subject><subject>Full Research Paper</subject><subject>nitrenes</subject><subject>photochemical cyclization</subject><issn>1860-5397</issn><issn>2195-951X</issn><issn>1860-5397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpdkttrFDEUhwdR7EVf_ANkwJdWzJr75UWQorZQ7IP6HHI5s5tldrJOZsVd8H83262l9SUJJx8fh3N-TfOK4BlTkr73yxxmhM60fNIcEy0xEsyopw_eR81JKUuMOZZYPm-OqGIcc6WPmz_ftsO0gJJKm7uWviPIw7BLJf92u9wDYmfk8hzlAUrrt613BdAKYnITxHa9yFMOC1il4Pr2K7ppfR4i6vK4SsO8DdvQp52bUh5u3cjtUsx7fU6hdSHF8qJ51rm-wMu7-7T58fnT94tLdH3z5eri4zUKXNEJATgsO-076RRX0YdgDPE-6k4rDcZ5JZUWTPFaE0JGZQSJRDEqOzDECXbaXB28MbulXY9p5catzS7Z20Ie59aNUwo9WC4waKN01DJyuvcSDLwekuiO-q66Phxc642vowgwTKPrH0kf_wxpYef5l-UGUyx4FZzdCcb8cwNlsqtUAvS9GyBviiXKGCHq6nRF3_yHLvNmHOqoLDGCcUoYVpV6e6DCmEsZobtvhmC7T4jdJ8QSarWs8OuH7d-j_yLB_gKvAbcg</recordid><startdate>20160504</startdate><enddate>20160504</enddate><creator>Dzhons, Daria Yu</creator><creator>Budruev, Andrei V</creator><general>Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</general><general>Beilstein-Institut</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BFMQW</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>LK8</scope><scope>M2P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20160504</creationdate><title>Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids</title><author>Dzhons, Daria Yu ; Budruev, Andrei V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>1,5-electrocyclization</topic><topic>2,1-benzisoxazolones</topic><topic>aryl azides</topic><topic>azepinones</topic><topic>Chemistry</topic><topic>Full Research Paper</topic><topic>nitrenes</topic><topic>photochemical cyclization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dzhons, Daria Yu</creatorcontrib><creatorcontrib>Budruev, Andrei V</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Continental Europe Database</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Biological Science Collection</collection><collection>Science Database</collection><collection>Biological Science Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Beilstein journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dzhons, Daria Yu</au><au>Budruev, Andrei V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids</atitle><jtitle>Beilstein journal of organic chemistry</jtitle><addtitle>Beilstein J Org Chem</addtitle><date>2016-05-04</date><risdate>2016</risdate><volume>12</volume><issue>1</issue><spage>874</spage><epage>881</epage><pages>874-881</pages><issn>1860-5397</issn><issn>2195-951X</issn><eissn>1860-5397</eissn><abstract>The base-mediated photochemical cyclization of 2-azidobenzoic acids with the formation of 2,1-benzisoxazole-3(1H)-ones is reported. The optimization and scope of this cyclization reaction is discussed. It is shown that an essential step of the ring closure of 2-azidobenzoic acids is the formation and photolysis of 2-azidobenzoate anions.</abstract><cop>Germany</cop><pub>Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</pub><pmid>27340478</pmid><doi>10.3762/bjoc.12.86</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1860-5397
ispartof Beilstein journal of organic chemistry, 2016-05, Vol.12 (1), p.874-881
issn 1860-5397
2195-951X
1860-5397
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_450e8978d86d42678510e4510618f2bf
source Publicly Available Content Database; PubMed Central
subjects 1,5-electrocyclization
2,1-benzisoxazolones
aryl azides
azepinones
Chemistry
Full Research Paper
nitrenes
photochemical cyclization
title Synthesis of 2,1-benzisoxazole-3(1H)-ones by base-mediated photochemical N-O bond-forming cyclization of 2-azidobenzoic acids
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T19%3A36%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%202,1-benzisoxazole-3(1H)-ones%20by%20base-mediated%20photochemical%20N-O%20bond-forming%20cyclization%20of%202-azidobenzoic%20acids&rft.jtitle=Beilstein%20journal%20of%20organic%20chemistry&rft.au=Dzhons,%20Daria%20Yu&rft.date=2016-05-04&rft.volume=12&rft.issue=1&rft.spage=874&rft.epage=881&rft.pages=874-881&rft.issn=1860-5397&rft.eissn=1860-5397&rft_id=info:doi/10.3762/bjoc.12.86&rft_dat=%3Cproquest_doaj_%3E1799558608%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c472t-eea06f8bf6a747dbcc991bbd8f878e9ab76785374bbd556d7951d17326fe91a53%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1953421307&rft_id=info:pmid/27340478&rfr_iscdi=true