Double Smiles rearrangement of Passerini adducts towards benzoxazinones
A new straightforward access to benzoxazinones based on a three-component coupling is presented here. The mechanism of the whole process involves a double aryl transfer as clearly underlined by the X-ray diffraction analysis of the products.
Saved in:
Published in | Chemical communications (Cambridge, England) Vol. 50; no. 17; pp. 2214 - 2217 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
CAMBRIDGE
Royal Soc Chemistry
01.01.2014
Royal Society of Chemistry |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | A new straightforward access to benzoxazinones based on a three-component coupling is presented here. The mechanism of the whole process involves a double aryl transfer as clearly underlined by the X-ray diffraction analysis of the products. |
---|---|
AbstractList | A new straightforward access to benzoxazinones based on a three-component coupling is presented here. The mechanism of the whole process involves a double aryl transfer as clearly underlined by the X-ray diffraction analysis of the products. |
Author | Dos Santos, A. Martinand-Lurin, E. Retailleau, P. El Kaim, L. Grimaud, L. |
Author_xml | – sequence: 1 givenname: E. surname: Martinand-Lurin fullname: Martinand-Lurin, E. organization: Ecole Normale Super, Dept Chim, UPMC ENS CNRS UMR 8640, F-75231 Paris 05, France – sequence: 2 givenname: A. surname: Dos Santos fullname: Dos Santos, A. organization: ENSTA ParisTech, Ecole Polytech ENSTA CNRS, UMR 7652, Lab Chim & Proc, F-91120 Palaiseau, France – sequence: 3 givenname: L. surname: El Kaim fullname: El Kaim, L. email: laurent.elkaim@ensta-paristech.fr organization: ENSTA ParisTech, Ecole Polytech ENSTA CNRS, UMR 7652, Lab Chim & Proc, F-91120 Palaiseau, France – sequence: 4 givenname: L. orcidid: 0000-0003-3904-1822 surname: Grimaud fullname: Grimaud, L. email: laurence.grimaud@ens.fr organization: Ecole Normale Super, Dept Chim, UPMC ENS CNRS UMR 8640, F-75231 Paris 05, France – sequence: 5 givenname: P. surname: Retailleau fullname: Retailleau, P. organization: CNRS, Inst Chim Subst Nat, UPR 2301, Ctr Rech Gif Sur Yvette, F-91198 Gif Sur Yvette, France |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24435182$$D View this record in MEDLINE/PubMed https://hal.science/hal-00958815$$DView record in HAL |
BookMark | eNqNkMFKxDAQhoMorq5efADpVaWadJK2OUrVVVlQUMFbSdOpRnYTSbqu7tPbWt2zc5lh-P5h-HbJpnUWCTlg9JRRkGcatOaSJsnbBtlhkPJY8Px5s5-FjDPgYkR2Q3ijXTGRb5NRwjkIlic7ZHLhFtUMo4e5mWGIPCrvlX3BOdo2ck10r0JAb6yJVF0vdBui1i2Vr0NUoV25T7Uy_Tdhj2w1ahZw_7ePydPV5WNxHU_vJjfF-TTWIHgbS6SySUTDda1RSBCAIHPMNAOZYUohVRkkVQ1SU15pVjPOpeJZKqmsM85gTI6Gu69qVr57M1f-q3TKlNfn07LfUSpFnjPx0bPHA6u9C8Fjsw4wWvbmygKK4sfcbQcfDvD7oppjvUb_VHVAPgBLrFwTtEGrcY11agFolgnRTZwVplWtcbZwC9t20ZP_R-EbVIeKog |
CitedBy_id | crossref_primary_10_1002_anie_202116249 crossref_primary_10_1021_co5000882 crossref_primary_10_1002_ange_202116249 crossref_primary_10_1002_ejoc_201402783 crossref_primary_10_3390_molecules21091257 crossref_primary_10_1039_c4ob00475b crossref_primary_10_1039_D1OB02443D crossref_primary_10_1016_j_tetlet_2014_07_088 crossref_primary_10_1039_C9GC03173A crossref_primary_10_1021_jo502145v crossref_primary_10_1002_jccs_202200290 crossref_primary_10_1002_ejoc_202000536 crossref_primary_10_1002_chem_201701979 crossref_primary_10_1002_ejoc_201500222 |
Cites_doi | 10.1002/ejoc.200901264 10.1021/jo070202e 10.1021/ja903920J 10.1016/j.tetlet.2011.11.028 10.1002/poc.1298 10.1016/j.tetlet.2005.04.050 10.1016/j.tetlet.2008.09.070 10.1002/ejoc.200801117 10.1002/ejoc.201101684 10.1021/ol0617502 10.1002/anie.200502636 10.1007/s11030-009-9175-3 10.1039/c2gc36095k 10.1039/b808960d 10.1002/chem.200902911 10.1016/j.tet.2004.09.048 10.1080/00397910701863608 10.1007/128_049 10.1055/s-0029-1218789 10.1002/anie.200903790 10.1002/anie.201002919 10.1039/JR9300001327 10.1021/cr60153a002 10.1021/ja903920j 10.1070/RC1995v064n02ABEH000141 |
ContentType | Journal Article |
Copyright | Distributed under a Creative Commons Attribution 4.0 International License |
Copyright_xml | – notice: Distributed under a Creative Commons Attribution 4.0 International License |
DBID | 1KM 1KN BLEPL DTL GNMZZ NPM AAYXX CITATION 1XC |
DOI | 10.1039/c3cc49022j |
DatabaseName | Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2014 PubMed CrossRef Hyper Article en Ligne (HAL) |
DatabaseTitle | Web of Science PubMed CrossRef |
DatabaseTitleList | CrossRef PubMed Web of Science |
Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1364-548X |
EndPage | 2217 |
ExternalDocumentID | oai_HAL_hal_00958815v1 10_1039_C3CC49022J 24435182 000330775500041 |
Genre | Journal Article |
GrantInformation_xml | – fundername: ENSTA – fundername: ENS – fundername: CNRS; Centre National de la Recherche Scientifique (CNRS) |
GroupedDBID | --- -DZ -JG -~X 0-7 0R~ 1KM 1KN 29B 2WC 4.4 53G 5GY 6J9 705 70~ 7~J AAEMU AAHBH AAIWI AAJAE AAMEH AANOJ AAWGC AAXHV AAXPP ABASK ABDVN ABEMK ABJNI ABPDG ABRYZ ABXOH ACBEA ACGFO ACGFS ACIWK ACLDK ACNCT ADMRA ADSRN AEFDR AENEX AENGV AESAV AETIL AFLYV AFOGI AFRDS AFVBQ AGEGJ AGKEF AGRSR AGSTE AHGCF ALMA_UNASSIGNED_HOLDINGS ANBJS ANUXI APEMP ASKNT AUDPV AZFZN BLAPV BLEPL BSQNT C6K CS3 DTL DU5 EBS ECGLT EE0 EF- EJD F5P GGIMP GNO GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED H13 HZ~ H~N IDZ IH2 J3G J3H J3I M4U N9A O9- P2P R7B R7C R7D RAOCF RCNCU RIG ROL RPMJG RRA RRC RSCEA SJN SKA SKF SKH SLH TN5 TWZ UPT VH6 VQA WH7 X7L NPM 0UZ 186 1TJ 3EH 6TJ 71~ 9M8 AAYOK AAYXX ACHDF ACMRT AFFNX AHGXI AI. ANLMG ASPBG AVWKF BBWZM CAG CITATION COF EEHRC F20 FA8 FEDTE HVGLF IDY KC5 L-8 MVM NDZJH OHT R56 RCLXC RNS RRXOS UHB VH1 WHG XJT ZCG ZKB 1XC |
ID | FETCH-LOGICAL-c354t-9e09f25f4cdce59353e398e7c1397e6036a732bd39c04bc1d1449a476909d7413 |
ISICitedReferencesCount | 20 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000330775500041 |
ISSN | 1359-7345 |
IngestDate | Wed Oct 23 06:40:14 EDT 2024 Fri Aug 23 01:06:10 EDT 2024 Sat Sep 28 07:58:29 EDT 2024 Wed Sep 18 10:07:57 EDT 2024 Fri Oct 18 19:41:38 EDT 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 17 |
Keywords | ALDEHYDES ARYLATION |
Language | English |
License | Distributed under a Creative Commons Attribution 4.0 International License: http://creativecommons.org/licenses/by/4.0 |
LinkModel | OpenURL |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-c354t-9e09f25f4cdce59353e398e7c1397e6036a732bd39c04bc1d1449a476909d7413 |
ORCID | 0000-0003-3904-1822 0000-0003-3995-519X 0000-0001-5729-8010 |
PMID | 24435182 |
PageCount | 4 |
ParticipantIDs | webofscience_primary_000330775500041CitationCount crossref_primary_10_1039_C3CC49022J webofscience_primary_000330775500041 pubmed_primary_24435182 hal_primary_oai_HAL_hal_00958815v1 |
PublicationCentury | 2000 |
PublicationDate | 2014-01-01 |
PublicationDateYYYYMMDD | 2014-01-01 |
PublicationDate_xml | – month: 01 year: 2014 text: 2014-01-01 day: 01 |
PublicationDecade | 2010 |
PublicationPlace | CAMBRIDGE |
PublicationPlace_xml | – name: CAMBRIDGE – name: England |
PublicationTitle | Chemical communications (Cambridge, England) |
PublicationTitleAbbrev | CHEM COMMUN |
PublicationTitleAlternate | Chem Commun (Camb) |
PublicationYear | 2014 |
Publisher | Royal Soc Chemistry Royal Society of Chemistry |
Publisher_xml | – name: Royal Soc Chemistry – name: Royal Society of Chemistry |
References | Paixao, MW (WOS:000270436700006) 2009; 48 Warren, LA (WOS:000188153000185) 1930 Zajc, B (WOS:000278405600013) 2010 Plesniak, K (WOS:000246178600005) 2007; 275 El Kaim, L (WOS:000284598600027) 2010; 14 Aissa, C (WOS:000265464300001) 2009; 2009 Gerasimova, T. N. (000330775500041.10) 1995; 64 Jin, YL (WOS:000260843500026) 2008; 49 Koszelewski, D (WOS:000256530700015) 2008; 38 Wu, FL (WOS:000276742400019) 2010; 2010 Pruger, B (WOS:000276327300025) 2010; 16 Mironov, MA (WOS:000229484600002) 2005; 46 Shao, YD (WOS:000300930800017) 2012; 2012 Snape, TJ (WOS:000260309500009) 2008; 37 Rotas, G (WOS:000224953200003) 2004; 60 El Kaim, L (WOS:000234007700029) 2005; 44 Truce, W. E. (000330775500041.24) 1970; 18 Siddiqui, N. (000330775500041.21) 2010; 2 Warren, L. A. (000330775500041.26) 1930 Huang, XL (WOS:000284708400016) 2010; 49 GERASIMOVA, TN (WOS:A1994MV02500017) 1994; 66 El Kaim, L (WOS:000246570200024) 2007; 72 BUNNETT, JF (WOS:A1951UE94700002) 1951; 49 Cui, C (WOS:000310156300029) 2012; 14 Sun, H (WOS:000253690100006) 2008; 21 Bousquet, T (WOS:000299582100011) 2012; 53 Nielsen, M (WOS:000268644400054) 2009; 131 El Kaim, L (WOS:000241381800010) 2006; 8 El Kaïm (C3CC49022J-(cit5b)/*[position()=1]) 2007; 72 Nielsen (C3CC49022J-(cit3c)/*[position()=1]) 2009; 131 Plesniak (C3CC49022J-(cit2e)/*[position()=1]) 2007; 275 El Kaïm (C3CC49022J-(cit6)/*[position()=1]) 2006; 8 Shao (C3CC49022J-(cit3e)/*[position()=1]) 2012 Cui (C3CC49022J-(cit7c)/*[position()=1]) 2012; 14 Wu (C3CC49022J-(cit3g)/*[position()=1]) 2010 El Kaim (C3CC49022J-(cit5a)/*[position()=1]) 2005; 44 Warren (C3CC49022J-(cit1a)/*[position()=1]) 1930 Zajc (C3CC49022J-(cit4b)/*[position()=1]) 2010 Truce (C3CC49022J-(cit2b)/*[position()=1]) 1970; 18 Siddiqui (C3CC49022J-(cit11)/*[position()=2]) 2010; 2 Koszelewski (C3CC49022J-(cit7a)/*[position()=1]) 2008; 38 Paixão (C3CC49022J-(cit3d)/*[position()=1]) 2009; 48 Sun (C3CC49022J-(cit10)/*[position()=1]) 2008; 21 Prüger (C3CC49022J-(cit3f)/*[position()=1]) 2010; 16 Bousquet (C3CC49022J-(cit7b)/*[position()=1]) 2012; 53 Jin (C3CC49022J-(cit3b)/*[position()=1]) 2008; 49 Aïssa (C3CC49022J-(cit4a)/*[position()=1]) 2009 El Kaïm (C3CC49022J-(cit5c)/*[position()=1]) 2010; 14 Snape (C3CC49022J-(cit2f)/*[position()=1]) 2008; 37 Gerasimova (C3CC49022J-(cit2c)/*[position()=1]) 1994; 66 Rotas (C3CC49022J-(cit9)/*[position()=1]) 2004; 60 Bunnet (C3CC49022J-(cit2a)/*[position()=1]) 1951; 49 Huang (C3CC49022J-(cit3a)/*[position()=1]) 2010; 49 Warren (C3CC49022J-(cit1b)/*[position()=1]) 1930 Mironov (C3CC49022J-(cit8)/*[position()=1]) 2005; 46 Gerasimova (C3CC49022J-(cit2d)/*[position()=1]) 1995; 64 |
References_xml | – volume: 2010 start-page: 1989 year: 2010 ident: WOS:000276742400019 article-title: New Methodology for the Conversion of Epoxides to Alkenes publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200901264 contributor: fullname: Wu, FL – volume: 72 start-page: 4169 year: 2007 ident: WOS:000246570200024 article-title: Smiles rearrangements in Ugi- and Passerini-type couplings: New multicomponent access to O- and N-arylamides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo070202e contributor: fullname: El Kaim, L – volume: 131 start-page: 10581 year: 2009 ident: WOS:000268644400054 article-title: Asymmetric Organocatalytic Formal Alkynylation and Alkenylation of alpha,beta-Unsaturated Aldehydes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja903920J contributor: fullname: Nielsen, M – start-page: 1327 year: 1930 ident: WOS:000188153000185 article-title: Dehydro-2-naphtholsulphone publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: Warren, LA – volume: 66 start-page: 69 year: 1994 ident: WOS:A1994MV02500017 article-title: THE SMILES REARRANGEMENT IN THE POLYFLUOROAROMATIC SERIES publication-title: JOURNAL OF FLUORINE CHEMISTRY contributor: fullname: GERASIMOVA, TN – volume: 53 start-page: 306 year: 2012 ident: WOS:000299582100011 article-title: Fast and efficient solvent-free Passerini reaction publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2011.11.028 contributor: fullname: Bousquet, T – volume: 21 start-page: 215 year: 2008 ident: WOS:000253690100006 article-title: Theoretical evidence on O-N type smiles rearrangement mechanism: a computational study on the intramolecular cyclization of N-methyl-2-(2-chloropyridin-3-yloxy)-acetamide anion publication-title: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY doi: 10.1002/poc.1298 contributor: fullname: Sun, H – volume: 46 start-page: 3957 year: 2005 ident: WOS:000229484600002 article-title: Acceleration of the Passerini reaction in the presence of nucleophilic additives publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2005.04.050 contributor: fullname: Mironov, MA – volume: 49 start-page: 6835 year: 2008 ident: WOS:000260843500026 article-title: The first total synthesis of glycyrol publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2008.09.070 contributor: fullname: Jin, YL – volume: 2009 start-page: 1831 year: 2009 ident: WOS:000265464300001 article-title: Mechanistic Manifold and New Developments of the Julia-Kocienski Reaction publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200801117 contributor: fullname: Aissa, C – volume: 64 start-page: 133 year: 1995 ident: 000330775500041.10 publication-title: Russ. Chem. Rev. contributor: fullname: Gerasimova, T. N. – volume: 2012 start-page: 1590 year: 2012 ident: WOS:000300930800017 article-title: Stereoselective Olefination and Regiospecific Vicinal Difunctionalization of Imines with alpha-(Benzothiazol-2-ylsulfonyl) Carbonyl Compounds publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201101684 contributor: fullname: Shao, YD – volume: 8 start-page: 5021 year: 2006 ident: WOS:000241381800010 article-title: O-arylative Passerini reactions publication-title: ORGANIC LETTERS doi: 10.1021/ol0617502 contributor: fullname: El Kaim, L – volume: 44 start-page: 7961 year: 2005 ident: WOS:000234007700029 article-title: Phenol Ugi-smiles systems: strategies for the multicomponent N-arylation of primary amines with isocyanides, aldehydes, and phenols publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200502636 contributor: fullname: El Kaim, L – volume: 14 start-page: 855 year: 2010 ident: WOS:000284598600027 article-title: Ugi-Smiles couplings: new entries to N-aryl carboxamide derivatives publication-title: MOLECULAR DIVERSITY doi: 10.1007/s11030-009-9175-3 contributor: fullname: El Kaim, L – volume: 2 start-page: 309 year: 2010 ident: 000330775500041.21 publication-title: J. Chem. Pharm. Res. contributor: fullname: Siddiqui, N. – volume: 14 start-page: 3157 year: 2012 ident: WOS:000310156300029 article-title: Ultrasound-promoted sterically congested Passerini reactions under solvent-free conditions publication-title: GREEN CHEMISTRY doi: 10.1039/c2gc36095k contributor: fullname: Cui, C – start-page: 935 year: 1930 ident: 000330775500041.26 publication-title: J. Chem. Soc. contributor: fullname: Warren, L. A. – volume: 37 start-page: 2452 year: 2008 ident: WOS:000260309500009 article-title: A truce on the Smiles rearrangement: revisiting an old reaction-the Truce-Smiles rearrangement publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b808960d contributor: fullname: Snape, TJ – volume: 16 start-page: 3783 year: 2010 ident: WOS:000276327300025 article-title: Transition-Metal-Free Formal Sonogashira Coupling and alpha-Carbonyl Arylation Reactions publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200902911 contributor: fullname: Pruger, B – volume: 60 start-page: 10825 year: 2004 ident: WOS:000224953200003 article-title: Synthesis of 5-alkyl(or aryl)pyrrolo[1,2-a]quinoxalin-4(5H)-ones by denitrocyclisation of N-alkyl(or aryl)-1-(2-nitrophenyl)-1H-pyrrole-2-carboxamides. Evidence of a Smiles rearrangement publication-title: TETRAHEDRON doi: 10.1016/j.tet.2004.09.048 contributor: fullname: Rotas, G – volume: 38 start-page: 1120 year: 2008 ident: WOS:000256530700015 article-title: Solvent-free Passerini reactions publication-title: SYNTHETIC COMMUNICATIONS doi: 10.1080/00397910701863608 contributor: fullname: Koszelewski, D – volume: 275 start-page: 163 year: 2007 ident: WOS:000246178600005 article-title: The Smiles rearrangement and the Julia-Kocienski olefination reaction publication-title: SULFUR-MEDIATED REARRANGEMENTS II doi: 10.1007/128_049 contributor: fullname: Plesniak, K – start-page: 1822 year: 2010 ident: WOS:000278405600013 article-title: Synthesis of Fluoroolefins via Julia-Kocienski Olefination publication-title: SYNTHESIS-STUTTGART doi: 10.1055/s-0029-1218789 contributor: fullname: Zajc, B – volume: 48 start-page: 7338 year: 2009 ident: WOS:000270436700006 article-title: Trends in Organocatalytic Conjugate Addition to Enones: An Efficient Approach to Optically Active Alkynyl, Alkenyl, and Ketone Products publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200903790 contributor: fullname: Paixao, MW – volume: 49 start-page: 273 year: 1951 ident: WOS:A1951UE94700002 article-title: AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS publication-title: CHEMICAL REVIEWS contributor: fullname: BUNNETT, JF – volume: 49 start-page: 8979 year: 2010 ident: WOS:000284708400016 article-title: A Direct Ylide Transfer to Carbonyl Derivatives and Heteroaromatic Compounds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201002919 contributor: fullname: Huang, XL – volume: 18 start-page: 99 year: 1970 ident: 000330775500041.24 publication-title: Org. React. contributor: fullname: Truce, W. E. – start-page: 1989 year: 2010 ident: C3CC49022J-(cit3g)/*[position()=1] publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.200901264 contributor: fullname: Wu – start-page: 1822 year: 2010 ident: C3CC49022J-(cit4b)/*[position()=1] publication-title: Synthesis doi: 10.1055/s-0029-1218789 contributor: fullname: Zajc – volume: 53 start-page: 306 year: 2012 ident: C3CC49022J-(cit7b)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2011.11.028 contributor: fullname: Bousquet – start-page: 1327 year: 1930 ident: C3CC49022J-(cit1b)/*[position()=1] publication-title: J. Chem. Soc. doi: 10.1039/JR9300001327 contributor: fullname: Warren – volume: 49 start-page: 273 year: 1951 ident: C3CC49022J-(cit2a)/*[position()=1] publication-title: Chem. Rev. doi: 10.1021/cr60153a002 contributor: fullname: Bunnet – volume: 37 start-page: 2452 year: 2008 ident: C3CC49022J-(cit2f)/*[position()=1] publication-title: Chem. Soc. Rev. doi: 10.1039/b808960d contributor: fullname: Snape – volume: 48 start-page: 7338 year: 2009 ident: C3CC49022J-(cit3d)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200903790 contributor: fullname: Paixão – start-page: 1590 year: 2012 ident: C3CC49022J-(cit3e)/*[position()=1] publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201101684 contributor: fullname: Shao – volume: 49 start-page: 6835 year: 2008 ident: C3CC49022J-(cit3b)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2008.09.070 contributor: fullname: Jin – volume: 66 start-page: 69 year: 1994 ident: C3CC49022J-(cit2c)/*[position()=1] publication-title: Russ. Chem. Rev. contributor: fullname: Gerasimova – volume: 44 start-page: 7961 year: 2005 ident: C3CC49022J-(cit5a)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200502636 contributor: fullname: El Kaim – start-page: 935 year: 1930 ident: C3CC49022J-(cit1a)/*[position()=1] publication-title: J. Chem. Soc. contributor: fullname: Warren – volume: 72 start-page: 4169 year: 2007 ident: C3CC49022J-(cit5b)/*[position()=1] publication-title: J. Org. Chem. doi: 10.1021/jo070202e contributor: fullname: El Kaïm – volume: 8 start-page: 5021 year: 2006 ident: C3CC49022J-(cit6)/*[position()=1] publication-title: Org. Lett. doi: 10.1021/ol0617502 contributor: fullname: El Kaïm – volume: 38 start-page: 1120 year: 2008 ident: C3CC49022J-(cit7a)/*[position()=1] publication-title: Synth. Commun. doi: 10.1080/00397910701863608 contributor: fullname: Koszelewski – volume: 14 start-page: 855 year: 2010 ident: C3CC49022J-(cit5c)/*[position()=1] publication-title: Mol. Diversity doi: 10.1007/s11030-009-9175-3 contributor: fullname: El Kaïm – volume: 18 start-page: 99 year: 1970 ident: C3CC49022J-(cit2b)/*[position()=1] publication-title: Org. React. contributor: fullname: Truce – start-page: 1831 year: 2009 ident: C3CC49022J-(cit4a)/*[position()=1] publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.200801117 contributor: fullname: Aïssa – volume: 21 start-page: 215 year: 2008 ident: C3CC49022J-(cit10)/*[position()=1] publication-title: J. Phys. Org. Chem. doi: 10.1002/poc.1298 contributor: fullname: Sun – volume: 275 start-page: 163 year: 2007 ident: C3CC49022J-(cit2e)/*[position()=1] publication-title: Top. Curr. Chem. doi: 10.1007/128_049 contributor: fullname: Plesniak – volume: 49 start-page: 8979 year: 2010 ident: C3CC49022J-(cit3a)/*[position()=1] publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201002919 contributor: fullname: Huang – volume: 14 start-page: 3157 year: 2012 ident: C3CC49022J-(cit7c)/*[position()=1] publication-title: Green Chem. doi: 10.1039/c2gc36095k contributor: fullname: Cui – volume: 2 start-page: 309 year: 2010 ident: C3CC49022J-(cit11)/*[position()=2] publication-title: J. Chem. Pharm. Res. contributor: fullname: Siddiqui – volume: 46 start-page: 3957 year: 2005 ident: C3CC49022J-(cit8)/*[position()=1] publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2005.04.050 contributor: fullname: Mironov – volume: 131 start-page: 10581 year: 2009 ident: C3CC49022J-(cit3c)/*[position()=1] publication-title: J. Am. Chem. Soc. doi: 10.1021/ja903920j contributor: fullname: Nielsen – volume: 64 start-page: 133 year: 1995 ident: C3CC49022J-(cit2d)/*[position()=1] publication-title: Russ. Chem. Rev. doi: 10.1070/RC1995v064n02ABEH000141 contributor: fullname: Gerasimova – volume: 60 start-page: 10825 year: 2004 ident: C3CC49022J-(cit9)/*[position()=1] publication-title: Tetrahedron doi: 10.1016/j.tet.2004.09.048 contributor: fullname: Rotas – volume: 16 start-page: 3783 year: 2010 ident: C3CC49022J-(cit3f)/*[position()=1] publication-title: Chem.–Eur. J. doi: 10.1002/chem.200902911 contributor: fullname: Prüger |
SSID | ssj0000158 |
Score | 2.2728503 |
Snippet | A new straightforward access to benzoxazinones based on a three-component coupling is presented here. The mechanism of the whole process involves a double aryl... |
Source | Web of Science |
SourceID | hal crossref pubmed webofscience |
SourceType | Open Access Repository Aggregation Database Index Database Enrichment Source |
StartPage | 2214 |
SubjectTerms | Chemical Sciences Chemistry Chemistry, Multidisciplinary Organic chemistry Physical Sciences Science & Technology |
Title | Double Smiles rearrangement of Passerini adducts towards benzoxazinones |
URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000330775500041 https://www.ncbi.nlm.nih.gov/pubmed/24435182 https://hal.science/hal-00958815 |
Volume | 50 |
WOS | 000330775500041 |
WOSCitedRecordID | wos000330775500041 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1bb9MwFLZY9wAvE3c6Lopgb5Uhie3GfqxCWRkFIa2T-lY5jiOGWDu1KUL79ZwTJ6kzLhooUhQ5jiP5nBx9PvH3HUKOVJbDkQgqWSYpj2RBdWwkFZonQxFpUUjkO3_8NJyc8ZO5mF9jl5TZa3P1W17J_1gV2sCuyJL9B8u2g0IDXIN94QwWhvONbAzoF4lPpxfwaWP6X6_XyBVo_u9_1viv_Xx5PoDwssVdG2W1SXYzyOzyavUDlaVRqt8HqK2AgPGZI1VqtqV3VfHTFf_wEglOkADa6BQz-B2Ww9vVZnCK5Yo3nfTp-Nvgg3blnNsc9DHKX2zzXVudkoi4l5KwLoyyIaewFpr7cdYJzDb-lPhRM3ZE0l_CechQDdUwY7gCsPHV7wSmuLyoDAsIhYnI1TC6Jp7d3Noj-3GihOiR_dF49n7qKYwJ2ajWMvVm9ypUia4f7kCWvS-4YfZvaKVCJrO75KBeUgQj5x_3yC27vE9up00lvwfk2PlJ4Pwk6PhJsCqC1k-C2k-C2k-Crp88JGfvxrN0QusCGtQwwUuqbKiKWBTc5Mi2Y4JZpqRNDMJ-OwTwohMWZzlTJuSZiXJYXSv8SFWocoCa7BHp4fhPSIBlF3iYmRwgPoegrXMrdSi0LERmYi775FUzR4tLp5OyqPY3MLVIWZpWk3rSJy9h-toOKG0-GU0X2IZYX8pIfI_65LGb3bZfY4g-OfKnu72PC3uGWo5Y3YPDANFNuqW1CD6KP5SHf3zpU3Jn5-PPSK9cb-1zAKJl9qJ2pp9A4oa_ |
link.rule.ids | 230,315,786,790,891,27955,27956 |
linkProvider | Royal Society of Chemistry |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Double+Smiles+rearrangement+of+Passerini+adducts+towards+benzoxazinones&rft.jtitle=Chemical+communications+%28Cambridge%2C+England%29&rft.au=Martinand-Lurin%2C+E&rft.au=Dos+Santos%2C+A&rft.au=El+Kaim%2C+L&rft.au=Grimaud%2C+L&rft.date=2014-01-01&rft.eissn=1364-548X&rft.volume=50&rft.issue=17&rft.spage=2214&rft_id=info:doi/10.1039%2Fc3cc49022j&rft_id=info%3Apmid%2F24435182&rft.externalDocID=24435182 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1359-7345&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1359-7345&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1359-7345&client=summon |