Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives

A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N -2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to h...

Full description

Saved in:
Bibliographic Details
Published inChemical science (Cambridge) Vol. 13; no. 35; pp. 10448 - 10454
Main Authors Sun, Xi-Shang, Diao, Xin-Yu, Dong, Xiu-Qin, Wang, Chun-Jiang
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 15.08.2022
The Royal Society of Chemistry
Subjects
Alkynes
Chemistry
Diels-Alder reactions
Esters
Ferric ions
Reaction intermediates
Substrates
Online AccessGet full text

Cover

Abstract A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N -2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions.
AbstractList A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N -2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions. A serendipitous and efficient approach to access various δ-carbolines was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction in good to high yields with excellent regio/chemoselectivity.
A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N-2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions.
A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction of N -2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate tolerance. Importantly, the potential application of these fascinating δ-carboline derivative products is well demonstrated in the recognition of ferric ions.
Author Wang, Chun-Jiang
Dong, Xiu-Qin
Sun, Xi-Shang
Diao, Xin-Yu
Author_xml – sequence: 1
  givenname: Xi-Shang
  surname: Sun
  fullname: Sun, Xi-Shang
  organization: College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Wuhan University, Wuhan, Hubei, 430072, P. R. China
– sequence: 2
  givenname: Xin-Yu
  surname: Diao
  fullname: Diao, Xin-Yu
  organization: College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Wuhan University, Wuhan, Hubei, 430072, P. R. China
– sequence: 3
  givenname: Xiu-Qin
  orcidid: 0000-0002-5045-1198
  surname: Dong
  fullname: Dong, Xiu-Qin
  organization: College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Wuhan University, Wuhan, Hubei, 430072, P. R. China
– sequence: 4
  givenname: Chun-Jiang
  orcidid: 0000-0003-3629-6889
  surname: Wang
  fullname: Wang, Chun-Jiang
  organization: College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Wuhan University, Wuhan, Hubei, 430072, P. R. China, State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, P. R. China
BookMark eNpdkUtqHDEQhkWwIX5tcoKGbIxBGb2mu-VFwBnHDzBkkWQt1NXViYxamkg9A87KZ3BuEnIOHyIniewxBkcbqf76-ChRu2QrxICEvOHsHWdSz3qRgUle1_CK7AimOK3nUm89vwV7TQ5yvmblSMnnotkhdx9sRrpMcYwT9hXYDLbH6v43PaPo3eiCnVwMM_QIU4pwA9793ESnDn3-e_vrxPeYZglLm77IqoQWHtDjCofBgcMwVRYAc66mWN3_oWBTF70LWBXcrYt3jXmfbA_WZzx4uvfI17OPXxYX9OrT-eXi5IqCEmqizVDzTjDgArp20B3j3PbcMtZopVlJmVKlFKJvrejqeaOl7lUtGznnqLSUe-T9xrtcdSP2UKZL1ptlcqNNNyZaZ152gvtuvsW10ao4hCiCwydBij9WmCczugzovQ0YV9mIRrRcyVa0BX37H3odVymU7xWKK94qJppCHW0oSDHnhMPzMJyZhxWbU_F58bjihfwHx86gXA
CitedBy_id crossref_primary_10_1055_s_0042_1753085
crossref_primary_10_1007_s10593_023_03183_1
crossref_primary_10_1039_D3CC00520H
crossref_primary_10_1039_D4CC00060A
Cites_doi 10.1002/anie.201607918
10.1021/jm00171a015
10.1038/sj.onc.1209067
10.1039/C8RA01761A
10.1021/acs.orglett.9b04626
10.6023/cjoc202008023
10.1007/s11094-011-0641-8
10.1021/acs.orglett.8b03245
10.3762/bjoc.9.187
10.1007/978-1-4757-3061-6
10.1039/D1OB00153A
10.1038/sj.leu.2404652
10.1002/ajoc.202000690
10.1016/j.tet.2016.08.050
10.1039/D0SC04685J
10.1021/jm0010419
10.1021/bi301381h
10.1002/cber.19891220318
10.1039/C6CC09468F
10.1016/j.ejmech.2021.113536
10.1039/D0SC06162J
10.1039/C7CS00615B
10.1021/acs.orglett.1c00292
10.1007/BF00513842
10.1002/slct.202001149
10.1021/acs.joc.8b02293
10.1016/j.ccr.2008.03.008
10.2174/092986707779940998
10.1016/j.ejmech.2011.03.021
10.1039/C6TC00804F
10.1016/j.ejmech.2021.113321
10.2174/157017912801270568
10.1021/acs.orglett.0c01578
10.1021/acsami.9b20279
10.2174/1389557520666201001130114
10.1007/s10593-009-0373-9
10.1021/acs.joc.8b02112
10.1002/slct.202100181
10.1002/chem.201504416
10.1016/j.talanta.2015.02.013
10.1021/jm200448n
10.1021/acs.orglett.9b00021
10.1021/jm00386a003
10.1016/j.electacta.2013.11.025
10.1007/s10593-012-0939-9
10.1021/acs.orglett.9b01738
10.1016/j.bmc.2008.01.052
10.1039/C5OB02408K
10.1039/D0QO00519C
10.31635/ccschem.021.202100875
10.1021/np030392y
ContentType Journal Article
Copyright Copyright Royal Society of Chemistry 2022
This journal is © The Royal Society of Chemistry 2022 The Royal Society of Chemistry
Copyright_xml – notice: Copyright Royal Society of Chemistry 2022
– notice: This journal is © The Royal Society of Chemistry 2022 The Royal Society of Chemistry
DBID AAYXX
CITATION
7SR
8BQ
8FD
JG9
7X8
5PM
DOI 10.1039/d2sc03166c
DatabaseName CrossRef
Engineered Materials Abstracts
METADEX
Technology Research Database
Materials Research Database
MEDLINE - Academic
PubMed Central (Full Participant titles)
DatabaseTitle CrossRef
Materials Research Database
Engineered Materials Abstracts
Technology Research Database
METADEX
MEDLINE - Academic
DatabaseTitleList
Materials Research Database
CrossRef
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 2041-6539
EndPage 10454
ExternalDocumentID 10_1039_D2SC03166C
GrantInformation_xml – fundername: ;
  grantid: 2020CFA036; 2021CFA069
– fundername: ;
  grantid: 2042022kf1180
– fundername: ;
  grantid: BK20190213
– fundername: ;
  grantid: 22071186; 22071187
GroupedDBID -JG
0-7
0R~
53G
705
7~J
AAEMU
AAFWJ
AAIWI
AAJAE
AARTK
AAXHV
AAYXX
ABEMK
ABPDG
ABXOH
ACGFS
ACIWK
ADBBV
ADMRA
AEFDR
AENEX
AESAV
AFLYV
AFPKN
AGEGJ
AGRSR
AGSTE
AHGCF
AKBGW
ALMA_UNASSIGNED_HOLDINGS
ANUXI
AOIJS
APEMP
AUDPV
AZFZN
BCNDV
BLAPV
BSQNT
C6K
CITATION
D0L
EE0
EF-
F5P
GROUPED_DOAJ
H13
HYE
HZ~
H~N
O-G
O9-
OK1
PGMZT
R7C
R7D
RAOCF
RCNCU
RNS
RPM
RRC
RSCEA
RVUXY
SKA
SKF
SKH
SKJ
SKM
SKR
SKZ
SLC
SLF
SLH
SMJ
7SR
8BQ
8FD
JG9
7X8
5PM
ID FETCH-LOGICAL-c424t-7f61b20c12cb8f9b011ad1a007949012c0441a022d8a2b657939d4637351e4933
IEDL.DBID RPM
ISSN 2041-6520
IngestDate Tue Sep 17 21:31:41 EDT 2024
Fri Aug 16 22:46:17 EDT 2024
Thu Oct 10 17:23:40 EDT 2024
Fri Aug 23 01:58:36 EDT 2024
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 35
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c424t-7f61b20c12cb8f9b011ad1a007949012c0441a022d8a2b657939d4637351e4933
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
These authors contributed equally to this work.
ORCID 0000-0003-3629-6889
0000-0002-5045-1198
OpenAccessLink https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9473522/
PQID 2714184027
PQPubID 2047492
PageCount 7
ParticipantIDs pubmedcentral_primary_oai_pubmedcentral_nih_gov_9473522
proquest_miscellaneous_2728143828
proquest_journals_2714184027
crossref_primary_10_1039_D2SC03166C
PublicationCentury 2000
PublicationDate 2022-08-15
PublicationDateYYYYMMDD 2022-08-15
PublicationDate_xml – month: 08
  year: 2022
  text: 2022-08-15
  day: 15
PublicationDecade 2020
PublicationPlace Cambridge
PublicationPlace_xml – name: Cambridge
PublicationTitle Chemical science (Cambridge)
PublicationYear 2022
Publisher Royal Society of Chemistry
The Royal Society of Chemistry
Publisher_xml – name: Royal Society of Chemistry
– name: The Royal Society of Chemistry
References Liu (D2SC03166C/cit2f/1) 2007; 21
Doménech-Carbóa (D2SC03166C/cit11f/1) 2014; 115
Wen (D2SC03166C/cit3e/1) 2018; 83
Zhang (D2SC03166C/cit2a/1) 2016; 4
Alekseyev (D2SC03166C/cit1h/1) 2012; 47
Sako (D2SC03166C/cit1o/1) 2008; 16
Funke (D2SC03166C/cit2c/1) 2016; 22
Xiao (D2SC03166C/cit12/1) 2021; 12
Hwang (D2SC03166C/cit11a/1) 2020; 12
Welch (D2SC03166C/cit4/1) 1995
Zhang (D2SC03166C/cit5f/1) 2021; 41
Smith (D2SC03166C/cit6/1) 2001
Zhang (D2SC03166C/cit1f/1) 2021; 10
Zhou (D2SC03166C/cit2e/1) 2006; 25
Le Gresley (D2SC03166C/cit1r/1) 2016; 14
Aaghaz (D2SC03166C/cit1c/1) 2021; 216
Subbaraju (D2SC03166C/cit2d/1) 2004; 67
Lakowicz (D2SC03166C/cit10/1) 1999
Jiang (D2SC03166C/cit2h/1) 2016; 72
Smirnova (D2SC03166C/cit1i/1) 2011; 45
Faheem (D2SC03166C/cit1d/1) 2021; 21
Zhu (D2SC03166C/cit5d/1) 2020; 22
Trudell (D2SC03166C/cit1k/1) 1987; 30
Riechert-Krause (D2SC03166C/cit2g/1) 2013; 52
Cao (D2SC03166C/cit1n/1) 2007; 14
Yang (D2SC03166C/cit8/1) 2018; 47
Trudell (D2SC03166C/cit1l/1) 1990; 33
Arzel (D2SC03166C/cit2i/1) 2001; 44
Kamboj (D2SC03166C/cit1a/1) 2021; 221
Tewari (D2SC03166C/cit1e/1) 2021; 6
Sun (D2SC03166C/cit5c/1) 2020; 11
Mazu (D2SC03166C/cit2b/1) 2011; 46
Yang (D2SC03166C/cit3c/1) 2017; 53
Rajesh (D2SC03166C/cit3f/1) 2020; 22
Semenov (D2SC03166C/cit1j/1) 1984; 20
Chen (D2SC03166C/cit5a/1) 2016; 55
Chen (D2SC03166C/cit3d/1) 2018; 20
Chang (D2SC03166C/cit1m/1) 2022; 4
Brunner (D2SC03166C/cit9a/1) 1989; 122
Lai (D2SC03166C/cit9c/1) 2020; 7
Alekseyev (D2SC03166C/cit1p/1) 2009; 45
Yao (D2SC03166C/cit1b/1) 2021; 19
Moon (D2SC03166C/cit11b/1) 2018; 8
Selvaraj (D2SC03166C/cit3a/1) 2018; 83
Radulescu (D2SC03166C/cit11e/1) 2015; 137
Shi (D2SC03166C/cit5b/1) 2019; 21
Gupta (D2SC03166C/cit1g/1) 2012; 9
Takeuchi (D2SC03166C/cit1q/1) 2011; 54
Singh (D2SC03166C/cit11c/1) 2020; 5
Zhang (D2SC03166C/cit3b/1) 2019; 21
Fan (D2SC03166C/cit11d/1) 2009; 253
Shimizu (D2SC03166C/cit9b/1) 2013; 9
Jang (D2SC03166C/cit5e/1) 2021; 23
References_xml – start-page: 311
  volume-title: General Features of Biological Activity of Fluorinated Amino Acids: Design, Pharmacology and Biochemistry
  year: 1995
  ident: D2SC03166C/cit4/1
  contributor:
    fullname: Welch
– volume: 55
  start-page: 13316
  year: 2016
  ident: D2SC03166C/cit5a/1
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.201607918
  contributor:
    fullname: Chen
– volume: 33
  start-page: 2412
  year: 1990
  ident: D2SC03166C/cit1l/1
  publication-title: J. Med. Chem.
  doi: 10.1021/jm00171a015
  contributor:
    fullname: Trudell
– volume: 25
  start-page: 503
  year: 2006
  ident: D2SC03166C/cit2e/1
  publication-title: Oncogene
  doi: 10.1038/sj.onc.1209067
  contributor:
    fullname: Zhou
– volume: 8
  start-page: 17025
  year: 2018
  ident: D2SC03166C/cit11b/1
  publication-title: RSC Adv.
  doi: 10.1039/C8RA01761A
  contributor:
    fullname: Moon
– volume: 22
  start-page: 1117
  year: 2020
  ident: D2SC03166C/cit3f/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.9b04626
  contributor:
    fullname: Rajesh
– volume: 41
  start-page: 669
  year: 2021
  ident: D2SC03166C/cit5f/1
  publication-title: Chin. J. Org. Chem.
  doi: 10.6023/cjoc202008023
  contributor:
    fullname: Zhang
– volume: 45
  start-page: 389
  year: 2011
  ident: D2SC03166C/cit1i/1
  publication-title: Pharm. Chem. J.
  doi: 10.1007/s11094-011-0641-8
  contributor:
    fullname: Smirnova
– volume: 20
  start-page: 7811
  year: 2018
  ident: D2SC03166C/cit3d/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.8b03245
  contributor:
    fullname: Chen
– volume: 9
  start-page: 1637
  year: 2013
  ident: D2SC03166C/cit9b/1
  publication-title: Beilstein J. Org. Chem.
  doi: 10.3762/bjoc.9.187
  contributor:
    fullname: Shimizu
– volume-title: Principles of Fluorescence Spectroscopy
  year: 1999
  ident: D2SC03166C/cit10/1
  doi: 10.1007/978-1-4757-3061-6
  contributor:
    fullname: Lakowicz
– volume: 19
  start-page: 3509
  year: 2021
  ident: D2SC03166C/cit1b/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/D1OB00153A
  contributor:
    fullname: Yao
– volume: 21
  start-page: 1300
  year: 2007
  ident: D2SC03166C/cit2f/1
  publication-title: Leukemia
  doi: 10.1038/sj.leu.2404652
  contributor:
    fullname: Liu
– volume: 10
  start-page: 429
  year: 2021
  ident: D2SC03166C/cit1f/1
  publication-title: Asian J. Org. Chem.
  doi: 10.1002/ajoc.202000690
  contributor:
    fullname: Zhang
– volume: 72
  start-page: 6444
  year: 2016
  ident: D2SC03166C/cit2h/1
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2016.08.050
  contributor:
    fullname: Jiang
– volume-title: March's Advanced Organic Chemistry-Reaction, Mechanism, and Structure
  year: 2001
  ident: D2SC03166C/cit6/1
  contributor:
    fullname: Smith
– volume: 11
  start-page: 10984
  year: 2020
  ident: D2SC03166C/cit5c/1
  publication-title: Chem. Sci.
  doi: 10.1039/D0SC04685J
  contributor:
    fullname: Sun
– volume: 44
  start-page: 949
  year: 2001
  ident: D2SC03166C/cit2i/1
  publication-title: J. Med. Chem.
  doi: 10.1021/jm0010419
  contributor:
    fullname: Arzel
– volume: 52
  start-page: 41
  year: 2013
  ident: D2SC03166C/cit2g/1
  publication-title: Biochemistry
  doi: 10.1021/bi301381h
  contributor:
    fullname: Riechert-Krause
– volume: 122
  start-page: 499
  year: 1989
  ident: D2SC03166C/cit9a/1
  publication-title: Chem. Ber.
  doi: 10.1002/cber.19891220318
  contributor:
    fullname: Brunner
– volume: 53
  start-page: 1676
  year: 2017
  ident: D2SC03166C/cit3c/1
  publication-title: Chem. Commun.
  doi: 10.1039/C6CC09468F
  contributor:
    fullname: Yang
– volume: 221
  start-page: 113536
  year: 2021
  ident: D2SC03166C/cit1a/1
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2021.113536
  contributor:
    fullname: Kamboj
– volume: 12
  start-page: 2940
  year: 2021
  ident: D2SC03166C/cit12/1
  publication-title: Chem. Sci.
  doi: 10.1039/D0SC06162J
  contributor:
    fullname: Xiao
– volume: 47
  start-page: 1783
  year: 2018
  ident: D2SC03166C/cit8/1
  publication-title: Chem. Soc. Rev.
  doi: 10.1039/C7CS00615B
  contributor:
    fullname: Yang
– volume: 23
  start-page: 1510
  year: 2021
  ident: D2SC03166C/cit5e/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.1c00292
  contributor:
    fullname: Jang
– volume: 20
  start-page: 345
  year: 1984
  ident: D2SC03166C/cit1j/1
  publication-title: Chem. Heterocycl. Compd.
  doi: 10.1007/BF00513842
  contributor:
    fullname: Semenov
– volume: 5
  start-page: 5172
  year: 2020
  ident: D2SC03166C/cit11c/1
  publication-title: ChemistrySelect
  doi: 10.1002/slct.202001149
  contributor:
    fullname: Singh
– volume: 83
  start-page: 15043
  year: 2018
  ident: D2SC03166C/cit3a/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.8b02293
  contributor:
    fullname: Selvaraj
– volume: 253
  start-page: 410
  year: 2009
  ident: D2SC03166C/cit11d/1
  publication-title: Coord. Chem. Rev.
  doi: 10.1016/j.ccr.2008.03.008
  contributor:
    fullname: Fan
– volume: 14
  start-page: 479
  year: 2007
  ident: D2SC03166C/cit1n/1
  publication-title: Curr. Med. Chem.
  doi: 10.2174/092986707779940998
  contributor:
    fullname: Cao
– volume: 46
  start-page: 2378
  year: 2011
  ident: D2SC03166C/cit2b/1
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2011.03.021
  contributor:
    fullname: Mazu
– volume: 4
  start-page: 4226
  year: 2016
  ident: D2SC03166C/cit2a/1
  publication-title: J. Mater. Chem. C
  doi: 10.1039/C6TC00804F
  contributor:
    fullname: Zhang
– volume: 216
  start-page: 113321
  year: 2021
  ident: D2SC03166C/cit1c/1
  publication-title: Eur. J. Med. Chem.
  doi: 10.1016/j.ejmech.2021.113321
  contributor:
    fullname: Aaghaz
– volume: 9
  start-page: 377
  year: 2012
  ident: D2SC03166C/cit1g/1
  publication-title: Curr. Org. Synth.
  doi: 10.2174/157017912801270568
  contributor:
    fullname: Gupta
– volume: 22
  start-page: 5014
  year: 2020
  ident: D2SC03166C/cit5d/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.0c01578
  contributor:
    fullname: Zhu
– volume: 12
  start-page: 8485
  year: 2020
  ident: D2SC03166C/cit11a/1
  publication-title: ACS Appl. Mater. Interfaces
  doi: 10.1021/acsami.9b20279
  contributor:
    fullname: Hwang
– volume: 21
  start-page: 398
  year: 2021
  ident: D2SC03166C/cit1d/1
  publication-title: Mini-Rev. Med. Chem.
  doi: 10.2174/1389557520666201001130114
  contributor:
    fullname: Faheem
– volume: 45
  start-page: 889
  year: 2009
  ident: D2SC03166C/cit1p/1
  publication-title: Chem. Heterocycl. Compd.
  doi: 10.1007/s10593-009-0373-9
  contributor:
    fullname: Alekseyev
– volume: 83
  start-page: 13308
  year: 2018
  ident: D2SC03166C/cit3e/1
  publication-title: J. Org. Chem.
  doi: 10.1021/acs.joc.8b02112
  contributor:
    fullname: Wen
– volume: 6
  start-page: 2428
  year: 2021
  ident: D2SC03166C/cit1e/1
  publication-title: ChemistrySelect
  doi: 10.1002/slct.202100181
  contributor:
    fullname: Tewari
– volume: 22
  start-page: 3170
  year: 2016
  ident: D2SC03166C/cit2c/1
  publication-title: Chem.–Eur. J.
  doi: 10.1002/chem.201504416
  contributor:
    fullname: Funke
– volume: 137
  start-page: 94
  year: 2015
  ident: D2SC03166C/cit11e/1
  publication-title: Talanta
  doi: 10.1016/j.talanta.2015.02.013
  contributor:
    fullname: Radulescu
– volume: 54
  start-page: 4839
  year: 2011
  ident: D2SC03166C/cit1q/1
  publication-title: J. Med. Chem.
  doi: 10.1021/jm200448n
  contributor:
    fullname: Takeuchi
– volume: 21
  start-page: 1331
  year: 2019
  ident: D2SC03166C/cit3b/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.9b00021
  contributor:
    fullname: Zhang
– volume: 30
  start-page: 456
  year: 1987
  ident: D2SC03166C/cit1k/1
  publication-title: J. Med. Chem.
  doi: 10.1021/jm00386a003
  contributor:
    fullname: Trudell
– volume: 115
  start-page: 546
  year: 2014
  ident: D2SC03166C/cit11f/1
  publication-title: Electrochim. Acta
  doi: 10.1016/j.electacta.2013.11.025
  contributor:
    fullname: Doménech-Carbóa
– volume: 47
  start-page: 1469
  year: 2012
  ident: D2SC03166C/cit1h/1
  publication-title: Chem. Heterocycl. Compd.
  doi: 10.1007/s10593-012-0939-9
  contributor:
    fullname: Alekseyev
– volume: 21
  start-page: 4842
  year: 2019
  ident: D2SC03166C/cit5b/1
  publication-title: Org. Lett.
  doi: 10.1021/acs.orglett.9b01738
  contributor:
    fullname: Shi
– volume: 16
  start-page: 3780
  year: 2008
  ident: D2SC03166C/cit1o/1
  publication-title: Bioorg. Med. Chem.
  doi: 10.1016/j.bmc.2008.01.052
  contributor:
    fullname: Sako
– volume: 14
  start-page: 3069
  year: 2016
  ident: D2SC03166C/cit1r/1
  publication-title: Org. Biomol. Chem.
  doi: 10.1039/C5OB02408K
  contributor:
    fullname: Le Gresley
– volume: 7
  start-page: 2263
  year: 2020
  ident: D2SC03166C/cit9c/1
  publication-title: Org. Chem. Front.
  doi: 10.1039/D0QO00519C
  contributor:
    fullname: Lai
– volume: 4
  start-page: 1414
  year: 2022
  ident: D2SC03166C/cit1m/1
  publication-title: CCS Chem
  doi: 10.31635/ccschem.021.202100875
  contributor:
    fullname: Chang
– volume: 67
  start-page: 461
  year: 2004
  ident: D2SC03166C/cit2d/1
  publication-title: J. Nat. Prod.
  doi: 10.1021/np030392y
  contributor:
    fullname: Subbaraju
SSID ssj0000331527
Score 2.4334922
Snippet A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade...
SourceID pubmedcentral
proquest
crossref
SourceType Open Access Repository
Aggregation Database
StartPage 10448
SubjectTerms Alkynes
Chemistry
Diels-Alder reactions
Esters
Ferric ions
Reaction intermediates
Substrates
Title Base-promoted cascade β-F-elimination/electrocyclization/Diels–Alder/retro-Diels–Alder reaction: efficient access to δ-carboline derivatives
URI https://www.proquest.com/docview/2714184027
https://search.proquest.com/docview/2728143828
https://pubmed.ncbi.nlm.nih.gov/PMC9473522
Volume 13
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LbtQwFL1qywI2iKcYKCMj2LqJH3mYXUkZVUhFCBg0rCK_IkaaZkYz00rd8Q3wJ4jv6EfwJVy7SWm2bGMntq6vc47le-8BeGVTZhppUioLIahslKelY5IWLuPSo4vpPCQ4n7zPj6fy3Syb7UDW58LEoH1r5gft4vSgnX-LsZWrU5v0cWLJh5NKBb1czpNd2MURbhzR4-9XiE6qlaeS0TzjaV-WVKjE8Y1FP85zOwSif-xyGBt5A2wm9-BuxxLJ4dVs7sOObx_A7aoXZ3sIP94g-tBVjKXzjli9CXHu5PIXnVC_iEpdweJJp3JjL-yiS7hMjuYIh3--_zwM-tzJ2mMzHTwjyCNjtsNr4mOBCZwj0VFYkWyX5PI3tXptgtiPJ9g9yqOd-80jmE7efq6OaSevQK3kckuLJmeGp5Zxa8pGGdzp2jGNpEFJZAncpkiVNGK8KzU3eYY7WTmZC7Q981IJ8Rj22mXrnwApdYFMyeIXCy9Z6RRiHkKjykqXqsbbEbzsbV2vrqpo1PH2W6j6iH-q4opUI9jvl6HudtKm5gWT4RTKixG8uG5Ga4eLDd365Vnow8sg487LERSD5bseLVTRHragc8Vq2p0zPf3vN5_BHR5yIkKd3Gwf9rbrM_8cmcrWjOMJfxz9cwy3Pn6Zzr7-BXOG8rw
link.rule.ids 230,315,733,786,790,870,891,27955,27956,53825,53827
linkProvider National Library of Medicine
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3NbtQwEB6VcigX_lEXChjB1ZvYcX7MraSsFuhWSLSot8h2HLFim13tZpHgxDPAmyCeow_BkzD2JqXhBteMncSeseezPDMfwDMTMl0JHVKRRhEVlbQ0K5mgaRlzYdHEVOISnCdHyfhEvD6NT7cg7nJhfNC-0dNhPTsb1tMPPrZycWaCLk4seDvJpePL5Ty4AldxvfL40iHdb8BR1JK18lAwmsQ87AqTRjIo-cqgJSeJ6buiP_iyHx15yd2MbsD77kc3USYfh-tGD82Xv2o4_vNIbsL1FoCS_Y34FmzZ-jbs5B3v2x349gIdG134MD1bEqNWLoSenP-gI2pnngTMKTNoCXTMZzNrczmDgyl62l9fv-876u9gaVFMe88IQlSfSPGcWF-7AgdPlOdsJM2cnP-kRi214xGyBJt75rVPdnUXTkYvj_MxbZkbqBFcNDStEqZ5aBg3Oqukxk1ElUwhHpECAQg3IaIwhfChzBTXSYybhCxFEuFkMCtkFN2D7Xpe210gmUoRhBl8Y2oFy0qJ7hS9royzMpSVNQN42imxWGwKdBT-Yj2SxQF_l3tV5wPY6_RbtIt0VfCUCXfA5ekAnlyIcbbdnYmq7Xzt2vDMMcTzbABpzy4uvuYKdPclqG1fqLvV7v3_7vkYdsbHk8Pi8NXRmwdwjbvUC1eON96D7Wa5tg8REDX6kTf_3xjAEfs
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LbtQwFLWgSMCGd8VAASPYehI7ThyzKxlG5dGqElSq2ER-RYyYZkYzGSRY8Q3wJ4jv6Ef0S3rtScqEZbex87rX9j2W7z0HoZcmprriOiZcJAnhlXQkt5QTYVPGHQwxlfkC5_2DbO-IvztOjzekvkLSvtGTYT09GdaTLyG3cn5ioi5PLDrcL6TXy2UsmtsquoquwZxlYmOjHhbhJGkFW1nMKclSFnfkpImMLFsaGM1ZZvrh6B_G7GdIboSc8W30ufvYdabJ1-Gq0UPz4z8ex0v9zR10qwWieHfd5S664up76EbR6b_dR79eQ4Aj85Cu5yw2aulT6fHpHzImbhrEwLxTo1ZIx3w307amMxpNIOKe_fy96yXAo4WDZtK7hgGqhoKKV9gFDgswAFZBuxE3M3z6lxi10F5PyGHoHhTYvrnlA3Q0fvOp2COtggMxnPGGiCqjmsWGMqPzSmpYTJSlCnCJ5ABEmIkBjSmAETZXTGcpLBbS8iwBg1DHZZJso616VruHCOdKABgz8EThOM2thLAK0VemuY1l5cwAvegcWc7XRB1lOGBPZDliH4vg7mKAdjofl-1kXZZMUO43ukwM0POLZrC2PztRtZutfB-We6V4lg-Q6I2Ni7d5ou5-C3g8EHa3Hn506TufoeuHo3H54e3B-8foJvMVGJ6VN91BW81i5Z4ALmr00zADzgF6IhR7
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=Base-promoted+cascade+%CE%B2-F-elimination%2Felectrocyclization%2FDiels%E2%80%93Alder%2Fretro-Diels%E2%80%93Alder+reaction%3A+efficient+access+to+%CE%B4-carboline+derivatives&rft.jtitle=Chemical+science+%28Cambridge%29&rft.au=Xi-Shang%2C+Sun&rft.au=Xin-Yu+Diao&rft.au=Xiu-Qin+Dong&rft.au=Chun-Jiang%2C+Wang&rft.date=2022-08-15&rft.pub=Royal+Society+of+Chemistry&rft.issn=2041-6520&rft.eissn=2041-6539&rft.volume=13&rft.issue=35&rft.spage=10448&rft.epage=10454&rft_id=info:doi/10.1039%2Fd2sc03166c&rft.externalDBID=NO_FULL_TEXT
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=2041-6520&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=2041-6520&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=2041-6520&client=summon