Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements

Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadduct...

Full description

Saved in:
Bibliographic Details
Published in:Organic & biomolecular chemistry 2003-08, Vol.1 (15), p.2689-2698
Main Authors: Roussel, Christophe, Fihi, Rachid, Ciamala, Kabula, Vebrel, Joël, Zair, Touria, Riche, Claude
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-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93
cites cdi_FETCH-LOGICAL-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93
container_end_page 2698
container_issue 15
container_start_page 2689
container_title Organic & biomolecular chemistry
container_volume 1
creator Roussel, Christophe
Fihi, Rachid
Ciamala, Kabula
Vebrel, Joël
Zair, Touria
Riche, Claude
description Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.
doi_str_mv 10.1039/b300628j
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_73606178</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>73606178</sourcerecordid><originalsourceid>FETCH-LOGICAL-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93</originalsourceid><addsrcrecordid>eNpFkE1LxDAURYMojo6Cv0C6EjfVpGmTZqmDnwy4UNclTV-mHZpkTFKk_96OM-jqXXjnnsVF6ILgG4KpuK0pxiwr1wfohOScp7ig4vAvZ3iGTkNYY0wEZ_kxmpFM5CUR9ARt3jeddy1E8E6NqoeQaO9M4kGq2DmbOJ3YLnpnp893F9vEQGzHHiykK2mMTOshjt71E_7LSNskwRnYFmMLnd-qvJd2BQZsDGfoSMs-wPn-ztHn48PH4jldvj29LO6WqcqEiKkgSrKMS8YFazgUQuclzokSutC6mUKmmeY6Y7WkGSkbwbmWULAacyrrRtA5utp5N959DRBiZbqgoO-lBTeEilOGGeHlBF7vQOVdCB50tfGdkX6sCK6261b3u3VfJ_Ry7xxqA80_uJ-T_gCN_Her</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>73606178</pqid></control><display><type>article</type><title>Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements</title><source>Royal Society of Chemistry: Jisc Collections: Journals Archive 1841-2007 (2019-2023)</source><creator>Roussel, Christophe ; Fihi, Rachid ; Ciamala, Kabula ; Vebrel, Joël ; Zair, Touria ; Riche, Claude</creator><creatorcontrib>Roussel, Christophe ; Fihi, Rachid ; Ciamala, Kabula ; Vebrel, Joël ; Zair, Touria ; Riche, Claude</creatorcontrib><description>Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b300628j</identifier><identifier>PMID: 12948193</identifier><language>eng</language><publisher>England</publisher><ispartof>Organic &amp; biomolecular chemistry, 2003-08, Vol.1 (15), p.2689-2698</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93</citedby><cites>FETCH-LOGICAL-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12948193$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Roussel, Christophe</creatorcontrib><creatorcontrib>Fihi, Rachid</creatorcontrib><creatorcontrib>Ciamala, Kabula</creatorcontrib><creatorcontrib>Vebrel, Joël</creatorcontrib><creatorcontrib>Zair, Touria</creatorcontrib><creatorcontrib>Riche, Claude</creatorcontrib><title>Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNpFkE1LxDAURYMojo6Cv0C6EjfVpGmTZqmDnwy4UNclTV-mHZpkTFKk_96OM-jqXXjnnsVF6ILgG4KpuK0pxiwr1wfohOScp7ig4vAvZ3iGTkNYY0wEZ_kxmpFM5CUR9ARt3jeddy1E8E6NqoeQaO9M4kGq2DmbOJ3YLnpnp893F9vEQGzHHiykK2mMTOshjt71E_7LSNskwRnYFmMLnd-qvJd2BQZsDGfoSMs-wPn-ztHn48PH4jldvj29LO6WqcqEiKkgSrKMS8YFazgUQuclzokSutC6mUKmmeY6Y7WkGSkbwbmWULAacyrrRtA5utp5N959DRBiZbqgoO-lBTeEilOGGeHlBF7vQOVdCB50tfGdkX6sCK6261b3u3VfJ_Ry7xxqA80_uJ-T_gCN_Her</recordid><startdate>20030807</startdate><enddate>20030807</enddate><creator>Roussel, Christophe</creator><creator>Fihi, Rachid</creator><creator>Ciamala, Kabula</creator><creator>Vebrel, Joël</creator><creator>Zair, Touria</creator><creator>Riche, Claude</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20030807</creationdate><title>Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements</title><author>Roussel, Christophe ; Fihi, Rachid ; Ciamala, Kabula ; Vebrel, Joël ; Zair, Touria ; Riche, Claude</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Roussel, Christophe</creatorcontrib><creatorcontrib>Fihi, Rachid</creatorcontrib><creatorcontrib>Ciamala, Kabula</creatorcontrib><creatorcontrib>Vebrel, Joël</creatorcontrib><creatorcontrib>Zair, Touria</creatorcontrib><creatorcontrib>Riche, Claude</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Roussel, Christophe</au><au>Fihi, Rachid</au><au>Ciamala, Kabula</au><au>Vebrel, Joël</au><au>Zair, Touria</au><au>Riche, Claude</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2003-08-07</date><risdate>2003</risdate><volume>1</volume><issue>15</issue><spage>2689</spage><epage>2698</epage><pages>2689-2698</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Cycloaddition of nitrones 1 with methylene-gamma-butyrolactones 2, 3 and 4 afforded spiroadducts 5, 6 and 7 with high selectivity. Mixtures of diastereoisomers were usually obtained, whose structures were established by 1H and 13C NMR spectroscopies or X-ray crystallography. Treatment of spiroadducts in acidic and alkaline media led to different, unexpected and novel rearrangements.</abstract><cop>England</cop><pmid>12948193</pmid><doi>10.1039/b300628j</doi><tpages>10</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2003-08, Vol.1 (15), p.2689-2698
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_73606178
source Royal Society of Chemistry: Jisc Collections: Journals Archive 1841-2007 (2019-2023)
title Spiroheterocycles from reaction of nitrones with methylene-gamma-butyrolactones and some of their rearrangements
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T23%3A54%3A20IST&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=Spiroheterocycles%20from%20reaction%20of%20nitrones%20with%20methylene-gamma-butyrolactones%20and%20some%20of%20their%20rearrangements&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Roussel,%20Christophe&rft.date=2003-08-07&rft.volume=1&rft.issue=15&rft.spage=2689&rft.epage=2698&rft.pages=2689-2698&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/b300628j&rft_dat=%3Cproquest_cross%3E73606178%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c299t-91ca627a6796d7e59f48041c9f5ffd41c2f6f7f26ba3218d977fae56b073abd93%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=73606178&rft_id=info:pmid/12948193&rfr_iscdi=true