Gold-Catalyzed Intramolecular Regioselective 7-exo-dig Cyclization To Access 3-Methylene-3,4-dihydrobenzo[b]oxepinones

An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were ob...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-01, Vol.19 (1), p.282-285
Main Authors: Mangina, N S V M Rao, Kadiyala, Veerabhushanam, Guduru, Ravinder, Goutham, Kommuru, Sridhar, Balasubramanian, Karunakar, Galla V
Format: Article
Language:English
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-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43
cites cdi_FETCH-LOGICAL-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43
container_end_page 285
container_issue 1
container_start_page 282
container_title Organic letters
container_volume 19
creator Mangina, N S V M Rao
Kadiyala, Veerabhushanam
Guduru, Ravinder
Goutham, Kommuru
Sridhar, Balasubramanian
Karunakar, Galla V
description An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were obtained in good to excellent yields in a one-pot synthesis at ambient temperature.
doi_str_mv 10.1021/acs.orglett.6b03433
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1851694733</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1851694733</sourcerecordid><originalsourceid>FETCH-LOGICAL-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43</originalsourceid><addsrcrecordid>eNo9kF9LwzAUxYMobk4_gSB99MHMpEn653EMnYOJIPNJpKTp3VZJm5mkY92nt7K6p3vu5Zx7uT-EbikZUxLSR6nc2Ni1Bu_HUU4YZ-wMDakIGY6JCM9POiIDdOXcNyG0m6SXaBAmneahGKLdzOgCT6WXuj1AEcxrb2VlNKhGSxu8w7o0DrrWlzsIYgx7g4tyHUxbpcuD9KWpg6UJJkqBcwHDr-A3rYYaMHvgnXPTFtbkUB_MZ_5l9rAta1ODu0YXK6kd3PR1hD6en5bTF7x4m82nkwVWjAiPBVER756NgEqRS5HSiBMW51SoKGKpSkWSE5WqOBeCJ7KQnEquElbQEFZMcjZC98e9W2t-GnA-q0qnQGtZg2lcRhNBo5THjHVWdrQqa5yzsMq2tqykbTNKsj_gWQc864FnPfAuddcfaPIKilPmnzD7BTO3gEw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1851694733</pqid></control><display><type>article</type><title>Gold-Catalyzed Intramolecular Regioselective 7-exo-dig Cyclization To Access 3-Methylene-3,4-dihydrobenzo[b]oxepinones</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Mangina, N S V M Rao ; Kadiyala, Veerabhushanam ; Guduru, Ravinder ; Goutham, Kommuru ; Sridhar, Balasubramanian ; Karunakar, Galla V</creator><creatorcontrib>Mangina, N S V M Rao ; Kadiyala, Veerabhushanam ; Guduru, Ravinder ; Goutham, Kommuru ; Sridhar, Balasubramanian ; Karunakar, Galla V</creatorcontrib><description>An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were obtained in good to excellent yields in a one-pot synthesis at ambient temperature.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.6b03433</identifier><identifier>PMID: 28001425</identifier><language>eng</language><publisher>United States</publisher><ispartof>Organic letters, 2017-01, Vol.19 (1), p.282-285</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43</citedby><cites>FETCH-LOGICAL-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43</cites><orcidid>0000-0001-8971-8550</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28001425$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mangina, N S V M Rao</creatorcontrib><creatorcontrib>Kadiyala, Veerabhushanam</creatorcontrib><creatorcontrib>Guduru, Ravinder</creatorcontrib><creatorcontrib>Goutham, Kommuru</creatorcontrib><creatorcontrib>Sridhar, Balasubramanian</creatorcontrib><creatorcontrib>Karunakar, Galla V</creatorcontrib><title>Gold-Catalyzed Intramolecular Regioselective 7-exo-dig Cyclization To Access 3-Methylene-3,4-dihydrobenzo[b]oxepinones</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were obtained in good to excellent yields in a one-pot synthesis at ambient temperature.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNo9kF9LwzAUxYMobk4_gSB99MHMpEn653EMnYOJIPNJpKTp3VZJm5mkY92nt7K6p3vu5Zx7uT-EbikZUxLSR6nc2Ni1Bu_HUU4YZ-wMDakIGY6JCM9POiIDdOXcNyG0m6SXaBAmneahGKLdzOgCT6WXuj1AEcxrb2VlNKhGSxu8w7o0DrrWlzsIYgx7g4tyHUxbpcuD9KWpg6UJJkqBcwHDr-A3rYYaMHvgnXPTFtbkUB_MZ_5l9rAta1ODu0YXK6kd3PR1hD6en5bTF7x4m82nkwVWjAiPBVER756NgEqRS5HSiBMW51SoKGKpSkWSE5WqOBeCJ7KQnEquElbQEFZMcjZC98e9W2t-GnA-q0qnQGtZg2lcRhNBo5THjHVWdrQqa5yzsMq2tqykbTNKsj_gWQc864FnPfAuddcfaPIKilPmnzD7BTO3gEw</recordid><startdate>20170106</startdate><enddate>20170106</enddate><creator>Mangina, N S V M Rao</creator><creator>Kadiyala, Veerabhushanam</creator><creator>Guduru, Ravinder</creator><creator>Goutham, Kommuru</creator><creator>Sridhar, Balasubramanian</creator><creator>Karunakar, Galla V</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8971-8550</orcidid></search><sort><creationdate>20170106</creationdate><title>Gold-Catalyzed Intramolecular Regioselective 7-exo-dig Cyclization To Access 3-Methylene-3,4-dihydrobenzo[b]oxepinones</title><author>Mangina, N S V M Rao ; Kadiyala, Veerabhushanam ; Guduru, Ravinder ; Goutham, Kommuru ; Sridhar, Balasubramanian ; Karunakar, Galla V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mangina, N S V M Rao</creatorcontrib><creatorcontrib>Kadiyala, Veerabhushanam</creatorcontrib><creatorcontrib>Guduru, Ravinder</creatorcontrib><creatorcontrib>Goutham, Kommuru</creatorcontrib><creatorcontrib>Sridhar, Balasubramanian</creatorcontrib><creatorcontrib>Karunakar, Galla V</creatorcontrib><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>Mangina, N S V M Rao</au><au>Kadiyala, Veerabhushanam</au><au>Guduru, Ravinder</au><au>Goutham, Kommuru</au><au>Sridhar, Balasubramanian</au><au>Karunakar, Galla V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gold-Catalyzed Intramolecular Regioselective 7-exo-dig Cyclization To Access 3-Methylene-3,4-dihydrobenzo[b]oxepinones</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2017-01-06</date><risdate>2017</risdate><volume>19</volume><issue>1</issue><spage>282</spage><epage>285</epage><pages>282-285</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were obtained in good to excellent yields in a one-pot synthesis at ambient temperature.</abstract><cop>United States</cop><pmid>28001425</pmid><doi>10.1021/acs.orglett.6b03433</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-8971-8550</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2017-01, Vol.19 (1), p.282-285
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1851694733
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Gold-Catalyzed Intramolecular Regioselective 7-exo-dig Cyclization To Access 3-Methylene-3,4-dihydrobenzo[b]oxepinones
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T04%3A17%3A00IST&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=Gold-Catalyzed%20Intramolecular%20Regioselective%207-exo-dig%20Cyclization%20To%20Access%203-Methylene-3,4-dihydrobenzo%5Bb%5Doxepinones&rft.jtitle=Organic%20letters&rft.au=Mangina,%20N%20S%20V%20M%20Rao&rft.date=2017-01-06&rft.volume=19&rft.issue=1&rft.spage=282&rft.epage=285&rft.pages=282-285&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.6b03433&rft_dat=%3Cproquest_cross%3E1851694733%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c305t-50c641026e1a5ba59164037b15c6639c958b0c9c7b5548ada41a4c83d12ef3a43%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1851694733&rft_id=info:pmid/28001425&rfr_iscdi=true