Reaction of 1-substituted 3-aminoquinolinediones with isocyanic and isothiocyanic acid

Mrkvička, Vladimír; Rudolf, Ondřej; Lyčka, Antonín; Klásek, Antonín

dc.title	Reaction of 1-substituted 3-aminoquinolinediones with isocyanic and isothiocyanic acid	en
dc.contributor.author	Mrkvička, Vladimír
dc.contributor.author	Rudolf, Ondřej
dc.contributor.author	Lyčka, Antonín
dc.contributor.author	Klásek, Antonín
dc.relation.ispartof	Tetrahedron
dc.identifier.issn	0040-4020 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued	2011-04-01
utb.relation.volume	67
utb.relation.issue	13
dc.citation.spage	2407
dc.citation.epage	2413
dc.type	article
dc.language.iso	en
dc.publisher	Pergamon Elsevier Science Ltd.	en
dc.identifier.doi	10.1016/j.tet.2011.02.002
dc.relation.uri	https://www.sciencedirect.com/science/article/pii/S0040402011001682
dc.subject	alpha-Aminoketones	en
dc.subject	C-Debenzylation	en
dc.subject	Rearrangement	en
dc.subject	Thioxo group	en
dc.subject	Thiourea derivatives	en
dc.description.abstract	1-Substituted-3-aminoquinoline-2,4(1H,3H)-diones react with potassium cyanate or potassium thiocyanate in boiling acetic acid to give ureido- or thioureidooxindoles, spiro-oxindoles and dihydroimidazoquinolones. However, if the starting compounds are substituted with a benzyl group at position 3, a C-debenzylation proceeds to give imidazoquinolones. According to a proposed reaction mechanism, a molecular rearrangement of the primarily formed mono-substituted urea or thiourea takes place. All compounds were characterized by (1)H, (13)C and IR spectroscopy and MS data. (C) 2011 Elsevier Ltd. All rights reserved.	en
utb.faculty	Faculty of Technology
dc.identifier.uri	http://hdl.handle.net/10563/1002174
utb.identifier.rivid	RIV/70883521:28110/11:43865342!RIV12-MSM-28110___
utb.identifier.obdid	43865344
utb.identifier.scopus	2-s2.0-79952449304
utb.identifier.wok	000288841300005
utb.identifier.coden	TETRA
utb.source	j-wok
dc.date.accessioned	2011-08-16T15:06:36Z
dc.date.available	2011-08-16T15:06:36Z
utb.contributor.internalauthor	Mrkvička, Vladimír
utb.contributor.internalauthor	Rudolf, Ondřej
utb.contributor.internalauthor	Klásek, Antonín
utb.scopus.affiliation	Mrkvička V., Department of Chemistry, Faculty of Technology, Tomas Bata University, 762 72 Zlín, Czech Republic; Rudolf O., Department of Chemistry, Faculty of Technology, Tomas Bata University, 762 72 Zlín, Czech Republic; Lyčka A., Research Institute for Organic Syntheses (VUOS), 533 54 Pardubice 20, Rybitví 296, Czech Republic, University of Hradec Králové, Faculty of Education, CZ 500 03 Hradec, Rokitanského 62, Králové 3, Czech Republic; Klásek A., Department of Chemistry, Faculty of Technology, Tomas Bata University, 762 72 Zlín, Czech Republic