Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction

A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyz...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-11, Vol.355 (17), p.3401-3406
Main Authors: Ji, Fei, Lv, Mei-fang, Yi, Wen-bin, Cai, Chun
Format: Article
Language:English
Subjects:
1,4‐benzoxazepines
4-benzoxazepines
Accessibility
aziridine ring-opening
Catalysis
Derivatives
domino process
isocyanide-insertion
Natural products
regioselectivity
Synthesis
Transformations
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-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3
cites cdi_FETCH-LOGICAL-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3
container_end_page 3406
container_issue 17
container_start_page 3401
container_title Advanced synthesis & catalysis
container_volume 355
creator Ji, Fei
Lv, Mei-fang
Yi, Wen-bin
Cai, Chun
description A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyzed isocyanide‐insertion reaction. This regioselective and high‐yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles.
doi_str_mv 10.1002/adsc.201300650
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1671603111</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1671603111</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3</originalsourceid><addsrcrecordid>eNqFkDtPwzAUhSMEEs-V2SMDKdexYydjaaFUVCBRHqPlJjdgSO1ip4H219OqqGJjOmf4vjOcKDql0KEAyYUuQ9FJgDIAkcJOdEAFTWNORb677SnsR4chvANQmUl5ELXjhW3eMJhAXEXoOY8v0S7dt17izFgkffSm1Y1pMZDWaKLJnWuxJn03NdaR7tJ4U67BB2Nf4_sZ2lUSbUsyDK5YaGtKjIc2oG-Ms-QBdbEux9FepeuAJ795FD1dXz32buLR_WDY647iggsGcZZwTACLXHPJKskZE5lkjPNJQidykvISWcIgRylBVKUuZJ6XuaiqimsO2YQdRWeb3Zl3n3MMjZqaUGBda4tuHhQVkgpglNIV2tmghXcheKzUzJup9gtFQa0PVuuD1fbglZBvhC9T4-IfWnX7495fN964JjT4vXW1_1BCMpmql7uB6slxNrq9Gahn9gNnIo7N</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1671603111</pqid></control><display><type>article</type><title>Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Ji, Fei ; Lv, Mei-fang ; Yi, Wen-bin ; Cai, Chun</creator><creatorcontrib>Ji, Fei ; Lv, Mei-fang ; Yi, Wen-bin ; Cai, Chun</creatorcontrib><description>A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyzed isocyanide‐insertion reaction. This regioselective and high‐yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201300650</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>1,4‐benzoxazepines ; 4-benzoxazepines ; Accessibility ; aziridine ring-opening ; Catalysis ; Derivatives ; domino process ; isocyanide-insertion ; Natural products ; regioselectivity ; Synthesis ; Transformations</subject><ispartof>Advanced synthesis &amp; catalysis, 2013-11, Vol.355 (17), p.3401-3406</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3</citedby><cites>FETCH-LOGICAL-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,783,787,27938,27939</link.rule.ids></links><search><creatorcontrib>Ji, Fei</creatorcontrib><creatorcontrib>Lv, Mei-fang</creatorcontrib><creatorcontrib>Yi, Wen-bin</creatorcontrib><creatorcontrib>Cai, Chun</creatorcontrib><title>Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction</title><title>Advanced synthesis &amp; catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyzed isocyanide‐insertion reaction. This regioselective and high‐yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles.</description><subject>1,4‐benzoxazepines</subject><subject>4-benzoxazepines</subject><subject>Accessibility</subject><subject>aziridine ring-opening</subject><subject>Catalysis</subject><subject>Derivatives</subject><subject>domino process</subject><subject>isocyanide-insertion</subject><subject>Natural products</subject><subject>regioselectivity</subject><subject>Synthesis</subject><subject>Transformations</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAUhSMEEs-V2SMDKdexYydjaaFUVCBRHqPlJjdgSO1ip4H219OqqGJjOmf4vjOcKDql0KEAyYUuQ9FJgDIAkcJOdEAFTWNORb677SnsR4chvANQmUl5ELXjhW3eMJhAXEXoOY8v0S7dt17izFgkffSm1Y1pMZDWaKLJnWuxJn03NdaR7tJ4U67BB2Nf4_sZ2lUSbUsyDK5YaGtKjIc2oG-Ms-QBdbEux9FepeuAJ795FD1dXz32buLR_WDY647iggsGcZZwTACLXHPJKskZE5lkjPNJQidykvISWcIgRylBVKUuZJ6XuaiqimsO2YQdRWeb3Zl3n3MMjZqaUGBda4tuHhQVkgpglNIV2tmghXcheKzUzJup9gtFQa0PVuuD1fbglZBvhC9T4-IfWnX7495fN964JjT4vXW1_1BCMpmql7uB6slxNrq9Gahn9gNnIo7N</recordid><startdate>20131125</startdate><enddate>20131125</enddate><creator>Ji, Fei</creator><creator>Lv, Mei-fang</creator><creator>Yi, Wen-bin</creator><creator>Cai, Chun</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20131125</creationdate><title>Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction</title><author>Ji, Fei ; Lv, Mei-fang ; Yi, Wen-bin ; Cai, Chun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>1,4‐benzoxazepines</topic><topic>4-benzoxazepines</topic><topic>Accessibility</topic><topic>aziridine ring-opening</topic><topic>Catalysis</topic><topic>Derivatives</topic><topic>domino process</topic><topic>isocyanide-insertion</topic><topic>Natural products</topic><topic>regioselectivity</topic><topic>Synthesis</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ji, Fei</creatorcontrib><creatorcontrib>Lv, Mei-fang</creatorcontrib><creatorcontrib>Yi, Wen-bin</creatorcontrib><creatorcontrib>Cai, Chun</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ji, Fei</au><au>Lv, Mei-fang</au><au>Yi, Wen-bin</au><au>Cai, Chun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2013-11-25</date><risdate>2013</risdate><volume>355</volume><issue>17</issue><spage>3401</spage><epage>3406</epage><pages>3401-3406</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><notes>ArticleID:ADSC201300650</notes><notes>istex:63778EAB79FCE9A733DCAD1493B440DF519CB478</notes><notes>NUST research funding - No. 2011ZDJH07</notes><notes>ark:/67375/WNG-C7S8LKHG-V</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A novel and efficient domino process has been developed for the synthesis of 1,4‐benzoxazepine derivatives from a range of readily accessible N‐tosylaziridines, 2‐iodophenols and isocyanides. This process involves the aziridine ring‐opening reaction with 2‐iodophenol, followed by a palladium‐catalyzed isocyanide‐insertion reaction. This regioselective and high‐yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201300650</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2013-11, Vol.355 (17), p.3401-3406
issn 1615-4150
1615-4169
language eng
recordid cdi_proquest_miscellaneous_1671603111
source Wiley-Blackwell Read & Publish Collection
subjects 1,4‐benzoxazepines
4-benzoxazepines
Accessibility
aziridine ring-opening
Catalysis
Derivatives
domino process
isocyanide-insertion
Natural products
regioselectivity
Synthesis
Transformations
title Synthesis of 1,4-Benzoxazepine Derivatives via a Novel Domino Aziridine Ring-Opening and Isocyanide-Insertion Reaction
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-11-04T18%3A07%3A30IST&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=Synthesis%20of%201,4-Benzoxazepine%20Derivatives%20via%20a%20Novel%20Domino%20Aziridine%20Ring-Opening%20and%20Isocyanide-Insertion%20Reaction&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Ji,%20Fei&rft.date=2013-11-25&rft.volume=355&rft.issue=17&rft.spage=3401&rft.epage=3406&rft.pages=3401-3406&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201300650&rft_dat=%3Cproquest_cross%3E1671603111%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c4630-824e20ec9a473f74336873344b21b7b54de32309e7706fdac799d96fff4a408b3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1671603111&rft_id=info:pmid/&rfr_iscdi=true