Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine

A general synthesis of dibenzoxepine lactams has been developed using a one-pot Cu-catalyzed etherification/aldol condensation cascade reaction. The reaction of 4-hydroxyisoindolin-1-one with a wide range of 2-bromobenzaldehydes in the presence of a copper catalyst provided various aristoyagonine de...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2013-09, Vol.15 (18), p.4718-4721
Hauptverfasser:	Lim, Hye Sun, Choi, Young Lok, Heo, Jung-Nyoung
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Benzaldehydes - chemistry Benzoxepins - chemical synthesis Benzoxepins - chemistry Catalysis Copper - chemistry Isoquinolines - chemical synthesis Isoquinolines - chemistry Lactams - chemical synthesis Lactams - chemistry Molecular Structure Stereoisomerism
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	4721
container_issue	18
container_start_page	4718
container_title	Organic letters
container_volume	15
creator	Lim, Hye Sun Choi, Young Lok Heo, Jung-Nyoung
description	A general synthesis of dibenzoxepine lactams has been developed using a one-pot Cu-catalyzed etherification/aldol condensation cascade reaction. The reaction of 4-hydroxyisoindolin-1-one with a wide range of 2-bromobenzaldehydes in the presence of a copper catalyst provided various aristoyagonine derivatives in good yields.
doi_str_mv	10.1021/ol402036t
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1434742721</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1434742721</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-b791e904772c3d99b1041607c496575314487e1ebafd0d2668488347e25578693</originalsourceid><addsrcrecordid>eNptkc1O3DAURq2qqFDKgheovKlUFgHbceKE3SjQH2kkqgLr6Ca-oUYZO9hOYXikPmVdZjpSpa5sfTr36F59hBxzdsqZ4GdulEywvIyvyAEvRJ4pVojXu3_J9snbEO4Z4ymp35B9IRljteQH5Nf12sYfGEygbqAXpkP77J5wMhbpEvoIq0B_GqBAmzlrIMK4fkZNryxm31ykl2nWm8H0EI2zZ4tRu5E2zmq04SWiDYQeNNLvmGwpOKeLaRq3AzS6R_CaJgu9cUlO_1ln4U2Ibg13zqZ93pG9AcaAR9v3kNx-urxpvmTLq89fm8Uyg7ziMetUzbFmUinR57quO84kL5nqZV0Wqsi5lJVCjh0MmmlRlpWsqlwqFEWhqrLOD8nHjXfy7mHGENuVCT2OI1h0c2i5TLQUSvCEnmzQ3rsQPA7t5M0K_LrlrP1TTburJrHvt9q5W6HekX-7SMCHDQB9aO_d7G268j-i364Plps</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1434742721</pqid></control><display><type>article</type><title>Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine</title><source>MEDLINE</source><source>ACS Publications</source><creator>Lim, Hye Sun ; Choi, Young Lok ; Heo, Jung-Nyoung</creator><creatorcontrib>Lim, Hye Sun ; Choi, Young Lok ; Heo, Jung-Nyoung</creatorcontrib><description>A general synthesis of dibenzoxepine lactams has been developed using a one-pot Cu-catalyzed etherification/aldol condensation cascade reaction. The reaction of 4-hydroxyisoindolin-1-one with a wide range of 2-bromobenzaldehydes in the presence of a copper catalyst provided various aristoyagonine derivatives in good yields.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol402036t</identifier><identifier>PMID: 24000941</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Aldehydes - chemistry ; Benzaldehydes - chemistry ; Benzoxepins - chemical synthesis ; Benzoxepins - chemistry ; Catalysis ; Copper - chemistry ; Isoquinolines - chemical synthesis ; Isoquinolines - chemistry ; Lactams - chemical synthesis ; Lactams - chemistry ; Molecular Structure ; Stereoisomerism</subject><ispartof>Organic letters, 2013-09, Vol.15 (18), p.4718-4721</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-b791e904772c3d99b1041607c496575314487e1ebafd0d2668488347e25578693</citedby><cites>FETCH-LOGICAL-a381t-b791e904772c3d99b1041607c496575314487e1ebafd0d2668488347e25578693</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/ol402036t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol402036t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24000941$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lim, Hye Sun</creatorcontrib><creatorcontrib>Choi, Young Lok</creatorcontrib><creatorcontrib>Heo, Jung-Nyoung</creatorcontrib><title>Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A general synthesis of dibenzoxepine lactams has been developed using a one-pot Cu-catalyzed etherification/aldol condensation cascade reaction. The reaction of 4-hydroxyisoindolin-1-one with a wide range of 2-bromobenzaldehydes in the presence of a copper catalyst provided various aristoyagonine derivatives in good yields.</description><subject>Aldehydes - chemistry</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzoxepins - chemical synthesis</subject><subject>Benzoxepins - chemistry</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - chemistry</subject><subject>Lactams - chemical synthesis</subject><subject>Lactams - chemistry</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1O3DAURq2qqFDKgheovKlUFgHbceKE3SjQH2kkqgLr6Ca-oUYZO9hOYXikPmVdZjpSpa5sfTr36F59hBxzdsqZ4GdulEywvIyvyAEvRJ4pVojXu3_J9snbEO4Z4ymp35B9IRljteQH5Nf12sYfGEygbqAXpkP77J5wMhbpEvoIq0B_GqBAmzlrIMK4fkZNryxm31ykl2nWm8H0EI2zZ4tRu5E2zmq04SWiDYQeNNLvmGwpOKeLaRq3AzS6R_CaJgu9cUlO_1ln4U2Ibg13zqZ93pG9AcaAR9v3kNx-urxpvmTLq89fm8Uyg7ziMetUzbFmUinR57quO84kL5nqZV0Wqsi5lJVCjh0MmmlRlpWsqlwqFEWhqrLOD8nHjXfy7mHGENuVCT2OI1h0c2i5TLQUSvCEnmzQ3rsQPA7t5M0K_LrlrP1TTburJrHvt9q5W6HekX-7SMCHDQB9aO_d7G268j-i364Plps</recordid><startdate>20130920</startdate><enddate>20130920</enddate><creator>Lim, Hye Sun</creator><creator>Choi, Young Lok</creator><creator>Heo, Jung-Nyoung</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>20130920</creationdate><title>Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine</title><author>Lim, Hye Sun ; Choi, Young Lok ; Heo, Jung-Nyoung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-b791e904772c3d99b1041607c496575314487e1ebafd0d2668488347e25578693</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Aldehydes - chemistry</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzoxepins - chemical synthesis</topic><topic>Benzoxepins - chemistry</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Isoquinolines - chemical synthesis</topic><topic>Isoquinolines - chemistry</topic><topic>Lactams - chemical synthesis</topic><topic>Lactams - chemistry</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lim, Hye Sun</creatorcontrib><creatorcontrib>Choi, Young Lok</creatorcontrib><creatorcontrib>Heo, Jung-Nyoung</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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lim, Hye Sun</au><au>Choi, Young Lok</au><au>Heo, Jung-Nyoung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-09-20</date><risdate>2013</risdate><volume>15</volume><issue>18</issue><spage>4718</spage><epage>4721</epage><pages>4718-4721</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A general synthesis of dibenzoxepine lactams has been developed using a one-pot Cu-catalyzed etherification/aldol condensation cascade reaction. The reaction of 4-hydroxyisoindolin-1-one with a wide range of 2-bromobenzaldehydes in the presence of a copper catalyst provided various aristoyagonine derivatives in good yields.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24000941</pmid><doi>10.1021/ol402036t</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2013-09, Vol.15 (18), p.4718-4721
issn	1523-7060 1523-7052
language	eng
recordid	cdi_proquest_miscellaneous_1434742721
source	MEDLINE; ACS Publications
subjects	Aldehydes - chemistry Benzaldehydes - chemistry Benzoxepins - chemical synthesis Benzoxepins - chemistry Catalysis Copper - chemistry Isoquinolines - chemical synthesis Isoquinolines - chemistry Lactams - chemical synthesis Lactams - chemistry Molecular Structure Stereoisomerism
title	Synthesis of Dibenzoxepine Lactams via a Cu-Catalyzed One-Pot Etherification/Aldol Condensation Cascade Reaction: Application toward the Total Synthesis of Aristoyagonine
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-26T16%3A24%3A31IST&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%20Dibenzoxepine%20Lactams%20via%20a%20Cu-Catalyzed%20One-Pot%20Etherification/Aldol%20Condensation%20Cascade%20Reaction:%20Application%20toward%20the%20Total%20Synthesis%20of%20Aristoyagonine&rft.jtitle=Organic%20letters&rft.au=Lim,%20Hye%20Sun&rft.date=2013-09-20&rft.volume=15&rft.issue=18&rft.spage=4718&rft.epage=4721&rft.pages=4718-4721&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol402036t&rft_dat=%3Cproquest_cross%3E1434742721%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=1434742721&rft_id=info:pmid/24000941&rfr_iscdi=true