An Efficient One-Pot, Multicomponent Synthesis of 1, 3-Thiazolidin-4-Ones Using L-Proline as Catalyst in Water

An efficient methodology for the synthesis of 1,3-thiazolidin-4-ones using L-Proline as catalyst under aqueous conditions has been developed. The one-pot, multicomponent reaction of aromatic/heterocyclic aldehyde, aromatic amine and thioglycolic acid at room temperature give 1,3thiazolidin-4-ones in...

Full description

Saved in:
Bibliographic Details
Published inLetters in organic chemistry Vol. 19; no. 1; pp. 9 - 13
Main Authors Gadkari, Yatin U., Shanbhag, Rajesh D., Telvekar, Vikas N.
Format Journal Article
LanguageEnglish
Published SHARJAH Bentham Science Publ Ltd 01.01.2022
Subjects
Online AccessGet more information

Cover

Loading…
Abstract An efficient methodology for the synthesis of 1,3-thiazolidin-4-ones using L-Proline as catalyst under aqueous conditions has been developed. The one-pot, multicomponent reaction of aromatic/heterocyclic aldehyde, aromatic amine and thioglycolic acid at room temperature give 1,3thiazolidin-4-ones in moderate to good yields. Further, the current approach is notably greener than traditional methods, with an E-factor of 3.1 and an eco scale score of 96. The developed protocol offers several features, such as being simple, environmentally benign, energy-efficient, economic, mild conditions, shorter reaction time.
AbstractList An efficient methodology for the synthesis of 1,3-thiazolidin-4-ones using L-Proline as catalyst under aqueous conditions has been developed. The one-pot, multicomponent reaction of aromatic/heterocyclic aldehyde, aromatic amine and thioglycolic acid at room temperature give 1,3thiazolidin-4-ones in moderate to good yields. Further, the current approach is notably greener than traditional methods, with an E-factor of 3.1 and an eco scale score of 96. The developed protocol offers several features, such as being simple, environmentally benign, energy-efficient, economic, mild conditions, shorter reaction time.
Author Gadkari, Yatin U.
Telvekar, Vikas N.
Shanbhag, Rajesh D.
Author_xml – sequence: 1
  givenname: Yatin U.
  surname: Gadkari
  fullname: Gadkari, Yatin U.
  organization: Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India
– sequence: 2
  givenname: Rajesh D.
  surname: Shanbhag
  fullname: Shanbhag, Rajesh D.
  organization: Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India
– sequence: 3
  givenname: Vikas N.
  surname: Telvekar
  fullname: Telvekar, Vikas N.
  email: vikastelvekar@rediffmail.com
  organization: Inst Chem Technol, Dept Pharmaceut Sci & Technol, Mumbai 400019, Maharashtra, India
BookMark eNqNj91KAzEQhYNUsK2-Q7y20Ux-dy_LUn-g0oItXpbsbmIj22xpUqQ-vSn6AF7N4Zxv5jAjNAh9sAjdAr1noMUDSE1BFwoKpRQDClBCDri4QEMotCSKSTnIOnPkDF6hUYyflHLgJRuiMA145pxvvA0JL4Ilyz5N8OuxS77pd_vclv23U0hbG33EvcMwwZystt58951vfSCC5L2I19GHDzwny0P2g8Um4sok051iwj7gd5Ps4RpdOtNFe_M3x2j9OFtVz2S-eHqppnNS80IkYgqgDpSSTVG3DSsps8IxDsbVgvLCKGdAaS21NgpkThnIWtdaly2IVnI2Rne_d79s3bt4_q6xm_3B78zhtKGUaiF0qXlW9EwX_6crn0zyfaj6Y0jsB-5ecaw
CitedBy_id crossref_primary_10_1007_s12039_022_02087_5
crossref_primary_10_1002_slct_202204417
crossref_primary_10_1007_s11164_022_04858_8
crossref_primary_10_3390_molecules28227612
crossref_primary_10_1080_00304948_2023_2202107
crossref_primary_10_1007_s12039_023_02189_8
crossref_primary_10_1002_slct_202304488
Cites_doi 10.1039/c6gc02157c
10.1039/d0nj01351j
10.1002/anie.200400650
10.1016/j.tetlet.2011.01.143
10.1002/anie.200460548
10.1002/anie.201006515
10.2174/1570178614666171002145250
10.1080/00397911.2020.1741641
10.1016/j.molliq.2014.07.039
10.1039/c9gc02657f
10.1186/1860-5397-2-3
10.1016/j.cclet.2015.10.029
10.1016/j.ejmech.2009.07.026
10.1039/c2ra20171b
10.1002/qsar.200540190
10.1055/s-0036-1591534
10.1016/j.bmcl.2009.09.101
10.1039/c3gc41218k
10.1021/ar800214s
10.1016/j.tetlet.2009.06.091
10.1007/s11164-015-2010-9
10.1080/00397911.2019.1597124
10.1080/15533174.2014.988227
ContentType Journal Article
DBID 1KN
AHQBO
BLEPL
DTL
DOI 10.2174/1570178618666210119121734
DatabaseName Current Chemical Reactions
Web of Science - Science Citation Index Expanded - 2022
Web of Science Core Collection
Science Citation Index Expanded
DatabaseTitle Web of Science
DatabaseTitleList Web of Science
Database_xml – sequence: 1
  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 no_fulltext_linktorsrc
Discipline Chemistry
EISSN 1875-6255
EndPage 13
ExternalDocumentID 000744797300003
GrantInformation_xml – fundername: TEQIP-III
GroupedDBID .5.
0R~
1KN
29L
4.4
53G
5GY
AAEGP
AAVXF
ABEEF
ABJNI
ABVDF
ACGFS
AENEX
AFUQM
ALMA_UNASSIGNED_HOLDINGS
ANTIV
BLEPL
CS3
DTL
DU5
EBS
F5P
GH2
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
HZ~
IPNFZ
KCGFV
O9-
P2P
RIG
ID FETCH-LOGICAL-b384t-a810f1665c8bdc2902e4f231afb4038a6fa1677577a61502e215b7b779d14d532
ISICitedReferencesCount 11
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000744797300003
ISSN 1570-1786
IngestDate Fri Oct 11 20:02:38 EDT 2024
Wed Sep 18 10:34:08 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 1
Keywords DESIGN
Multicomponent reaction
L-proline
E-factor
economical
thiazolidinone
water
GREEN
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-b384t-a810f1665c8bdc2902e4f231afb4038a6fa1677577a61502e215b7b779d14d532
PageCount 5
ParticipantIDs webofscience_primary_000744797300003CitationCount
webofscience_primary_000744797300003
PublicationCentury 2000
PublicationDate 2022-01-01
PublicationDateYYYYMMDD 2022-01-01
PublicationDate_xml – month: 01
  year: 2022
  text: 2022-01-01
  day: 01
PublicationDecade 2020
PublicationPlace SHARJAH
PublicationPlace_xml – name: SHARJAH
PublicationTitle Letters in organic chemistry
PublicationTitleAbbrev LETT ORG CHEM
PublicationYear 2022
Publisher Bentham Science Publ Ltd
Publisher_xml – name: Bentham Science Publ Ltd
References Mahata, S (WOS:000437236700004) 2018; 15
Bhagat, SB (WOS:000429998900004) 2018; 29
Tierney, J (WOS:000266716400009) 2008; 14
Van Aken, K (WOS:000241018500001) 2006; 2
Chaudhari, M.A. (000744797300003.23) 2007; 17
Kumaravel, K (WOS:000271391400006) 2009; 13
Rawal, RK (WOS:000222596200022) 2004
Bhosle, MR (WOS:000466783100001) 2019; 49
Ganem, B (WOS:000264301000007) 2009; 42
Dalko, PI (WOS:000224424600007) 2004; 43
Gokhale, KM (WOS:000524028200001) 2020; 50
Notz, W. (000744797300003.7) 2008; 9
Prasad, D (WOS:000301459900078) 2012; 2
Sadashiva, CT (WOS:000272928600008) 2009; 44
Hatamjafari, F. (000744797300003.29) 2013; 29
Sadeghzadeh, SM (WOS:000345179500065) 2014; 199
Ruijter, E (WOS:000292642600004) 2011; 50
Gui, QW (WOS:000505605500011) 2020; 22
Zhang, XY (WOS:000271029600005) 2009; 19
Sheldon, RA (WOS:000391728900003) 2017; 19
Kumar, D (WOS:000325593600032) 2013; 15
Ramon, DJ (WOS:000227684200008) 2005; 44
Taghrir, H (WOS:000361918500017) 2016; 46
Gadkari, YU (WOS:000537294300001) 2020; 44
Yadav, AK (WOS:000268509000022) 2009; 50
Pang, HX (WOS:000374799400007) 2016; 27
Mironov, MA (WOS:000238548900002) 2006; 25
Yadav, JS (WOS:000223951900047) 2004; 33
Chaudhari, MA (WOS:000365743300065) 2015; 41
Silverberg, L.J. (000744797300003.2) 2013; 5
Sandhar, RK (WOS:000253957900020) 2008; 85
Pratap, UR (WOS:000288730900037) 2011; 52
References_xml – volume: 19
  start-page: 18
  year: 2017
  ident: WOS:000391728900003
  article-title: The E factor 25 years on: the rise of green chemistry and sustainability
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c6gc02157c
  contributor:
    fullname: Sheldon, RA
– volume: 44
  start-page: 8167
  year: 2020
  ident: WOS:000537294300001
  article-title: Concentrated solar radiation as a renewable heat source for a preparative-scale and solvent-free Biginelli reaction
  publication-title: NEW JOURNAL OF CHEMISTRY
  doi: 10.1039/d0nj01351j
  contributor:
    fullname: Gadkari, YU
– volume: 43
  start-page: 5138
  year: 2004
  ident: WOS:000224424600007
  article-title: In the golden age of organocatalysis
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200400650
  contributor:
    fullname: Dalko, PI
– volume: 52
  start-page: 1689
  year: 2011
  ident: WOS:000288730900037
  article-title: Saccharomyces cerevisiae catalyzed one-pot three component synthesis of 2,3-diaryl-4-thiazolidinones
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2011.01.143
  contributor:
    fullname: Pratap, UR
– volume: 44
  start-page: 1602
  year: 2005
  ident: WOS:000227684200008
  article-title: Asymmetric multicomponent reactions (AMCRs): The new frontier
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.200460548
  contributor:
    fullname: Ramon, DJ
– volume: 14
  start-page: 453
  year: 2008
  ident: WOS:000266716400009
  article-title: A SECOND STUDY - PREDICTING THE C-13 CHEMICAL SHIFTS FOR A SERIES OF SUBSTITUTED 3-(4-METHOXYPHENYL)-2-PHENYL-1,3-THIAZOLIDIN-4-ONES
  publication-title: HETEROCYCLIC COMMUNICATIONS
  contributor:
    fullname: Tierney, J
– volume: 50
  start-page: 6234
  year: 2011
  ident: WOS:000292642600004
  article-title: Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  doi: 10.1002/anie.201006515
  contributor:
    fullname: Ruijter, E
– volume: 13
  start-page: 1820
  year: 2009
  ident: WOS:000271391400006
  article-title: Multi-Component Reactions in Water
  publication-title: CURRENT ORGANIC CHEMISTRY
  contributor:
    fullname: Kumaravel, K
– volume: 15
  start-page: 665
  year: 2018
  ident: WOS:000437236700004
  article-title: Graphene Oxide Catalyzed C-N/C-S/[3+2] Cyclization Cascade for Green Synthesis of Thiazolidinone in Water
  publication-title: LETTERS IN ORGANIC CHEMISTRY
  doi: 10.2174/1570178614666171002145250
  contributor:
    fullname: Mahata, S
– volume: 50
  start-page: 1396
  year: 2020
  ident: WOS:000524028200001
  article-title: Silica chloride (SiO2-Cl) catalyzed one pot synthesis of 2,3-disubstituted-thiazolidin-4-one
  publication-title: SYNTHETIC COMMUNICATIONS
  doi: 10.1080/00397911.2020.1741641
  contributor:
    fullname: Gokhale, KM
– volume: 199
  start-page: 440
  year: 2014
  ident: WOS:000345179500065
  article-title: Ionic liquid immobilized on FeNi3 as catalysts for efficient, green, and one-pot synthesis of 1,3-thiazolidin-4-one
  publication-title: JOURNAL OF MOLECULAR LIQUIDS
  doi: 10.1016/j.molliq.2014.07.039
  contributor:
    fullname: Sadeghzadeh, SM
– volume: 22
  start-page: 118
  year: 2020
  ident: WOS:000505605500011
  article-title: The clean preparation of multisubstituted pyrroles under metal- and solvent-free conditions
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c9gc02657f
  contributor:
    fullname: Gui, QW
– volume: 2
  start-page: ARTN 3
  year: 2006
  ident: WOS:000241018500001
  article-title: EcoScale, a semi-quantitative tool to select an organic preparation based on economical and ecological parameters
  publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1186/1860-5397-2-3
  contributor:
    fullname: Van Aken, K
– volume: 17
  start-page: 5634
  year: 2007
  ident: 000744797300003.23
  publication-title: Bioorg. Med. Chem. Lett.
  contributor:
    fullname: Chaudhari, M.A.
– volume: 85
  start-page: 220
  year: 2008
  ident: WOS:000253957900020
  article-title: Synthesis and fungitoxicity of aldimines and 4-thiazolidinones derived from 4-bromoaniline
  publication-title: JOURNAL OF THE INDIAN CHEMICAL SOCIETY
  contributor:
    fullname: Sandhar, RK
– start-page: 368
  year: 2004
  ident: WOS:000222596200022
  article-title: An expeditious synthesis of thiazolidinones and metathiazanones
  publication-title: JOURNAL OF CHEMICAL RESEARCH
  contributor:
    fullname: Rawal, RK
– volume: 27
  start-page: 335
  year: 2016
  ident: WOS:000374799400007
  article-title: A catalysis study of mesoporous MCM-41 supported Schiff base and CuSO4 center dot 5H(2)O in a highly regioselective synthesis of 4-thiazolidinone derivatives from cyclocondensation of mercaptoacetic acid
  publication-title: CHINESE CHEMICAL LETTERS
  doi: 10.1016/j.cclet.2015.10.029
  contributor:
    fullname: Pang, HX
– volume: 44
  start-page: 4848
  year: 2009
  ident: WOS:000272928600008
  article-title: Synthesis and pharmacological evaluation of novel N-alkyl/aryl substituted thiazolidinone arecoline analogues as muscarinic receptor 1 agonist in Alzheimer's dementia models
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2009.07.026
  contributor:
    fullname: Sadashiva, CT
– volume: 33
  start-page: 1168
  year: 2004
  ident: WOS:000223951900047
  article-title: A novel L-proline catalyzed Biginelli reaction: One-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions
  publication-title: CHEMISTRY LETTERS
  contributor:
    fullname: Yadav, JS
– volume: 5
  start-page: 120
  year: 2013
  ident: 000744797300003.2
  publication-title: Int. J. Chem.,
  contributor:
    fullname: Silverberg, L.J.
– volume: 2
  start-page: 3133
  year: 2012
  ident: WOS:000301459900078
  article-title: DBSA catalyzed, one-pot three-component "on water" green protocol for the synthesis of 2,3-disubstituted 4-thiazolidinones
  publication-title: RSC ADVANCES
  doi: 10.1039/c2ra20171b
  contributor:
    fullname: Prasad, D
– volume: 25
  start-page: 423
  year: 2006
  ident: WOS:000238548900002
  article-title: Design of Multi-Component Reactions: From libraries of compounds to libraries of reactions
  publication-title: QSAR & COMBINATORIAL SCIENCE
  doi: 10.1002/qsar.200540190
  contributor:
    fullname: Mironov, MA
– volume: 29
  start-page: 93
  year: 2013
  ident: 000744797300003.29
  publication-title: Orient. J. Chem.
  contributor:
    fullname: Hatamjafari, F.
– volume: 29
  start-page: 874
  year: 2018
  ident: WOS:000429998900004
  article-title: L-Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1H-Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
  publication-title: SYNLETT
  doi: 10.1055/s-0036-1591534
  contributor:
    fullname: Bhagat, SB
– volume: 19
  start-page: 6280
  year: 2009
  ident: WOS:000271029600005
  article-title: Ionic liquid mediated and promoted eco-friendly preparation of thiazolidinone and pyrimidine nucleoside-thiazolidinone hybrids and their antiparasitic activities
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2009.09.101
  contributor:
    fullname: Zhang, XY
– volume: 15
  start-page: 2872
  year: 2013
  ident: WOS:000325593600032
  article-title: Supported protic acid-catalyzed synthesis of 2,3-disubstituted thiazolidin-4-ones: enhancement of the catalytic potential of protic acid by adsorption on solid supports
  publication-title: GREEN CHEMISTRY
  doi: 10.1039/c3gc41218k
  contributor:
    fullname: Kumar, D
– volume: 42
  start-page: 463
  year: 2009
  ident: WOS:000264301000007
  article-title: Strategies for Innovation in Multicomponent Reaction Design
  publication-title: ACCOUNTS OF CHEMICAL RESEARCH
  doi: 10.1021/ar800214s
  contributor:
    fullname: Ganem, B
– volume: 50
  start-page: 5031
  year: 2009
  ident: WOS:000268509000022
  article-title: An ionic liquid mediated one-pot synthesis of substituted thiazolidinones and benzimidazoles
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/j.tetlet.2009.06.091
  contributor:
    fullname: Yadav, AK
– volume: 41
  start-page: 10027
  year: 2015
  ident: WOS:000365743300065
  article-title: beta-Cyclodextrin-SO3H-catalyzed facile and highly efficient synthesis of 4-thiazolidinones under solvent free conditions
  publication-title: RESEARCH ON CHEMICAL INTERMEDIATES
  doi: 10.1007/s11164-015-2010-9
  contributor:
    fullname: Chaudhari, MA
– volume: 9
  start-page: 1589
  year: 2008
  ident: 000744797300003.7
  publication-title: Eur. J. Org. Chem
  contributor:
    fullname: Notz, W.
– volume: 49
  start-page: 1286
  year: 2019
  ident: WOS:000466783100001
  article-title: Tromethamine organocatalyzed efficient tandem-multicomponent synthesis of new thiazolyl-4-thiazolidinones in aqueous medium
  publication-title: SYNTHETIC COMMUNICATIONS
  doi: 10.1080/00397911.2019.1597124
  contributor:
    fullname: Bhosle, MR
– volume: 46
  start-page: 246
  year: 2016
  ident: WOS:000361918500017
  article-title: Preparation of 2,3-Diarylthiazolidin-4-One Derivatives Using Barium Molybdate Nanopowders
  publication-title: SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY
  doi: 10.1080/15533174.2014.988227
  contributor:
    fullname: Taghrir, H
SSID ssj0031392
Score 2.3526638
Snippet An efficient methodology for the synthesis of 1,3-thiazolidin-4-ones using L-Proline as catalyst under aqueous conditions has been developed. The one-pot,...
Source Web of Science
SourceID webofscience
SourceType Enrichment Source
Index Database
StartPage 9
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title An Efficient One-Pot, Multicomponent Synthesis of 1, 3-Thiazolidin-4-Ones Using L-Proline as Catalyst in Water
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000744797300003
Volume 19
WOS 000744797300003
WOSCitedRecordID wos000744797300003
hasFullText
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lj9MwELYKSMAF8dQuLxlpb1mXOnHi5lgKaMWjrKCF5bSyE0cJXVykFqTdf8a_Y8ZOQlqKVLhEVZwmTubL-JvJPAg5CFMhtIyAuQ3gbRJAYRl-TWMiyfgA1jfQiOgaeDtJjmbi1Ul80uv97EQtfV_pfnaxNa_kf6QK-0CumCX7D5JtTwo74DfIF7YgYdjuJOORxc7IlctpDN5Zw44XPvrC1dSAN31hceTDuQWaV1ce4XhAxKZlpS4WZxUsXUww-O8y8NEDb9ixa-RjsAPNGJ0750vXRuCTaiJ5m_Rplwnk4ml9b6gsyJr2cW1Yj8rnyiezf4ZJ22DWb306pbK6VE7VvFdfzLIMnreDU3P2w8x98PfHag5TmfS7Doow3HBQPIMbLdXXVlehe60TsuSUrhwwLpuS2H4f2FEMbLN4TVOnfyDSq920s3771NbNlQEtL3RSwKXwSljmLwFrF8vbwVDtT12rxr2xSraxi451CZlioX9XZ_YSnA-Z-etJQwEioNXuM3tzY1fJk3oOT_86g63Mx7Gc6U1yozZP6Mhj7RbpGXubXBs3Yr1D7MjSFnO0xtwhXUccbRFHFwXlh3Qb3qjDG23xRtWSNnijlaUOb3fJ7OWL6fiI1T07mI6GYsXUkA8KniRxNtR5FqaD0IgCbAhVaAHaQCWF4omUsZQKWxGEBiinllrKNOcij6PwHrlsYap7hOapGWYqQb4EtDcsVKw0mPPAn3liwFLYJwfdB3b6zZdnOd0Q0D7huxw2rkviYymI1f3dTv2AXP8N-IfkSgF6xTwCkrrSjx0gfgEEs4kH
link.rule.ids 786
linkProvider Clarivate
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=An+Efficient+One-Pot%2C+Multicomponent+Synthesis+of+1%2C+3-Thiazolidin-4-Ones+Using+L-Proline+as+Catalyst+in+Water&rft.jtitle=Letters+in+organic+chemistry&rft.au=Gadkari%2C+Yatin+U.&rft.au=Shanbhag%2C+Rajesh+D.&rft.au=Telvekar%2C+Vikas+N.&rft.date=2022-01-01&rft.pub=Bentham+Science+Publ+Ltd&rft.issn=1570-1786&rft.eissn=1875-6255&rft.volume=19&rft.issue=1&rft.spage=9&rft.epage=13&rft_id=info:doi/10.2174%2F1570178618666210119121734&rft.externalDBID=n%2Fa&rft.externalDocID=000744797300003
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1570-1786&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1570-1786&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1570-1786&client=summon