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:
Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 50; no. 17; pp. 2214 - 2217
Main Authors Martinand-Lurin, E., Dos Santos, A., El Kaim, L., Grimaud, L., Retailleau, P.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2014
Royal Society of Chemistry
Subjects
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Organic chemistry
Physical Sciences
Science & Technology
ALDEHYDES
ARYLATION
Online AccessGet full text

Cover

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