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...
Saved in:
Published in | Letters in organic chemistry Vol. 19; no. 1; pp. 9 - 13 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
SHARJAH
Bentham Science Publ Ltd
01.01.2022
|
Subjects | |
Online Access | Get 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 |