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Synthesis of 1,4-Benzodiazepine-2,5-diones by base promoted ring expansion of 3-aminoquinoline-2,4-diones

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dc.title Synthesis of 1,4-Benzodiazepine-2,5-diones by base promoted ring expansion of 3-aminoquinoline-2,4-diones en
dc.contributor.author Křemen, Filip
dc.contributor.author Gazvoda, Martin
dc.contributor.author Kafka, Stanislav
dc.contributor.author Proisl, Karel
dc.contributor.author Srholcová, Anna
dc.contributor.author Klásek, Antonín
dc.contributor.author Urankar, Damijana
dc.contributor.author Košmrlj, Janez
dc.relation.ispartof Journal of Organic Chemistry
dc.identifier.issn 0022-3263 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2017
utb.relation.volume 82
utb.relation.issue 1
dc.citation.spage 715
dc.citation.epage 722
dc.type article
dc.language.iso en
dc.publisher American Chemical Society (ACS)
dc.identifier.doi 10.1021/acs.joc.6b01497
dc.relation.uri http://pubs.acs.org/doi/full/10.1021/acs.joc.6b01497
dc.description.abstract An unprecedented reactivity of 3-aminoquinoline-2,4-diones is reported. Under basic conditions, these compounds undergo molecular rearrangement to furnish 1,4-benzodiazepine-2,5-diones. The transformations take place under mild reaction conditions by using 1,1,3,3-tetramethylguanidine, NaOEt, or benzyltrimethylammonium hydroxide as a base. A proposed mechanism of the rearrangement and the conformational equilibrium of 1,4-benzodiazepine-2,5-dione rings are discussed. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1006973
utb.identifier.obdid 43877038
utb.identifier.scopus 2-s2.0-85018509973
utb.identifier.wok 000391781900070
utb.identifier.pubmed 27787977
utb.identifier.coden JOCEA
utb.source j-wok
dc.date.accessioned 2017-07-13T14:50:28Z
dc.date.available 2017-07-13T14:50:28Z
dc.description.sponsorship TBU in Zlin [IGA/FT/2016/004]; Ministry of Education, Science, and Sport, Republic of Slovenia, the Slovenian Research Agency [P1-0230]
utb.contributor.internalauthor Křemen, Filip
utb.contributor.internalauthor Kafka, Stanislav
utb.contributor.internalauthor Proisl, Karel
utb.contributor.internalauthor Srholcová, Anna
utb.contributor.internalauthor Klásek, Antonín
utb.fulltext.affiliation Filip Křemen, †,# Martin Gazvoda, ‡,# Stanislav Kafka,* ,† Karel Proisl, † Anna Srholcová , † Antonín Klá sek, † Damijana Urankar, ‡ and Janez Koš mrlj* ,‡ † Department of Chemistry, Faculty of Technology, Tomas Bata University, Zlín 76272, Czech Republic ‡ Faculty of Chemistry and Chemical Technology, University of Ljubljana, Več na pot 113, Ljubljana SI 1000, Slovenia
utb.fulltext.dates Received: June 22, 2016 Published: October 27, 2016
utb.fulltext.sponsorship This work was financed by TBU in Zlín ́(internal grant no. IGA/FT/2016/004, funded from the resources of specific university research) and the Ministry of Education, Science, and Sport, Republic of Slovenia, the Slovenian Research Agency (grant: P1-0230). The authors are grateful to an anonymous reviewer for pointing out Triton B and Mrs. H. Geržová for (Faculty of Technology, Tomas Bata University in Zlín) technical assistance.
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