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

Křemen, Filip; Gazvoda, Martin; Kafka, Stanislav; Proisl, Karel; Srholcová, Anna; Klásek, Antonín; Urankar, Damijana; Košmrlj, Janez

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.