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Article: Stereoselective synthesis of multifunctionalized 1,2,4-triazolidines by a ruthenium porphyrin-catalyzed three-component coupling reaction

TitleStereoselective synthesis of multifunctionalized 1,2,4-triazolidines by a ruthenium porphyrin-catalyzed three-component coupling reaction
Authors
Keywords1,2,4-triazolidines
1,3-dipolar cycloadditions
Cytotoxicity
Human carcinoma
Ruthenium porphyrins
Issue Date2006
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley.com/bw/journal.asp?ref=1615-4150
Citation
Advanced Synthesis And Catalysis, 2006, v. 348 n. 16-17, p. 2391-2396 How to Cite?
AbstractMultifunctionalized 1,2,4-triazolidines have been synthesized by a ruthenium porphyrincatalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed the in situ generation of azomethine ylides from α-diazo esters and imines. Stereoselective 1,3-dipolar cycloaddition reactions of the azomethine ylides with dialkyl azodicarboxylates gave the corresponding 1,2,4-triazolidines in good yields (up to 85%). Using chiral 8-phenylmenthanol α-diazo ester as the carbenoid source, chiral 1,2,4-triazolidines have been obtained with good diastereoselectivity (up to 84% de). Some of the 1,2,4-triazolidines exhibited good cytotoxicity against human nasopharyngeal carcinoma (SUNE1) (IC50 = 10.4 μM) and human cervical carcinoma (Heia) (IC50 = 10.7 μM) cell lines. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
Persistent Identifierhttp://hdl.handle.net/10722/69482
ISSN
2015 Impact Factor: 6.453
2015 SCImago Journal Rankings: 2.729
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorWang, MZen_HK
dc.contributor.authorXu, HWen_HK
dc.contributor.authorLiu, Yen_HK
dc.contributor.authorWong, MKen_HK
dc.contributor.authorChe, CMen_HK
dc.date.accessioned2010-09-06T06:14:04Z-
dc.date.available2010-09-06T06:14:04Z-
dc.date.issued2006en_HK
dc.identifier.citationAdvanced Synthesis And Catalysis, 2006, v. 348 n. 16-17, p. 2391-2396en_HK
dc.identifier.issn1615-4150en_HK
dc.identifier.urihttp://hdl.handle.net/10722/69482-
dc.description.abstractMultifunctionalized 1,2,4-triazolidines have been synthesized by a ruthenium porphyrincatalyzed three-component coupling reaction. In a one-pot reaction, ruthenium porphyrins catalyzed the in situ generation of azomethine ylides from α-diazo esters and imines. Stereoselective 1,3-dipolar cycloaddition reactions of the azomethine ylides with dialkyl azodicarboxylates gave the corresponding 1,2,4-triazolidines in good yields (up to 85%). Using chiral 8-phenylmenthanol α-diazo ester as the carbenoid source, chiral 1,2,4-triazolidines have been obtained with good diastereoselectivity (up to 84% de). Some of the 1,2,4-triazolidines exhibited good cytotoxicity against human nasopharyngeal carcinoma (SUNE1) (IC50 = 10.4 μM) and human cervical carcinoma (Heia) (IC50 = 10.7 μM) cell lines. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.en_HK
dc.languageengen_HK
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley.com/bw/journal.asp?ref=1615-4150en_HK
dc.relation.ispartofAdvanced Synthesis and Catalysisen_HK
dc.subject1,2,4-triazolidinesen_HK
dc.subject1,3-dipolar cycloadditionsen_HK
dc.subjectCytotoxicityen_HK
dc.subjectHuman carcinomaen_HK
dc.subjectRuthenium porphyrinsen_HK
dc.titleStereoselective synthesis of multifunctionalized 1,2,4-triazolidines by a ruthenium porphyrin-catalyzed three-component coupling reactionen_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=1615-4150&volume=348&spage=2391&epage=2396&date=2006&atitle=Stereoselective+Synthesis+of+Multifunctionalized+1,2,4-Triazolidines+by+a+Ruthenium+Porphyrin-Catalyzed+Three-Component+Coupling+Reactionen_HK
dc.identifier.emailLiu, Y:lyg100@hku.hken_HK
dc.identifier.emailChe, CM:cmche@hku.hken_HK
dc.identifier.authorityLiu, Y=rp00749en_HK
dc.identifier.authorityChe, CM=rp00670en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/adsc.200600320en_HK
dc.identifier.scopuseid_2-s2.0-33845256893en_HK
dc.identifier.hkuros130234en_HK
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-33845256893&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume348en_HK
dc.identifier.issue16-17en_HK
dc.identifier.spage2391en_HK
dc.identifier.epage2396en_HK
dc.identifier.isiWOS:000242471700013-
dc.publisher.placeGermanyen_HK
dc.identifier.scopusauthoridWang, MZ=24328900000en_HK
dc.identifier.scopusauthoridXu, HW=7407450997en_HK
dc.identifier.scopusauthoridLiu, Y=8225912600en_HK
dc.identifier.scopusauthoridWong, MK=7403908449en_HK
dc.identifier.scopusauthoridChe, CM=7102442791en_HK

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