Novel ring contraction of 3-hydroxy-2,4 (1H,3H) -quinolinediones in aqueous alkali. The first convenient route to 2-hydroxyindoxyls

Kafka, Stanislav; Klásek, Antonín; Košmrlj, Janez

dc.title	Novel ring contraction of 3-hydroxy-2,4 (1H,3H) -quinolinediones in aqueous alkali. The first convenient route to 2-hydroxyindoxyls	en
dc.contributor.author	Kafka, Stanislav
dc.contributor.author	Klásek, Antonín
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	2001
utb.relation.volume	66
utb.relation.issue	19
dc.citation.spage	6394
dc.citation.epage	6399
dc.type	article
dc.language.iso	en
dc.publisher	American Chemical Society (ACS)	en
dc.identifier.doi	10.1021/jo015786d
dc.relation.uri	http://pubs.acs.org/doi/abs/10.1021/jo015786d
dc.subject	pseudomonas putida	cs
dc.subject	heterocykly	cs
dc.subject	oxidace	cs
dc.subject	deriváty	cs
dc.subject	indoly	cs
dc.subject	přesmyk	cs
dc.subject	3-hydroxy-1,2,3,4-tetrahydrochinolin-2,4-diony	cs
dc.subject	1,2-dihydro-3H-indol-3-ony	cs
dc.subject	hydrolýza	cs
dc.subject	inhibitory	cs
dc.subject	pseudomonas putida	en
dc.subject	heterocyclic rings	en
dc.subject	oxidation	en
dc.subject	derivatives	en
dc.subject	indoles	en
dc.subject	rearrangement	en
dc.subject	3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones	en
dc.subject	1,2-dihydro-3H-indol-3-ones	en
dc.subject	hydrolysis	en
dc.subject	inhibitors	en
dc.description.abstract	Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.	en
utb.faculty	Faculty of Technology
dc.identifier.uri	http://hdl.handle.net/10563/1000023
utb.identifier.rivid	RIV/70883521:28110/01:63500209
utb.identifier.obdid	11051740
utb.identifier.scopus	2-s2.0-0035929447
utb.identifier.wok	000171100400028
utb.source	j-riv
utb.contributor.internalauthor	Kafka, Stanislav
utb.contributor.internalauthor	Klásek, Antonín
utb.fulltext.affiliation	Stanislav Kafka,,† Antonín Klásek,† and Janez Košmrlj,‡ Faculty of Technology, Tomas Bata University, 762 72 Zlín, Czech Republic, and Faculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000 Ljubljana, Slovenia janez.kosmrlj@uni-lj.si † Tomas Bata University. ‡ University of Ljubljana.
utb.fulltext.dates	Received May 23, 2001 Published on Web 08/24/2001
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utb.fulltext.sponsorship	The Ministry of Education, Youth and Sports of the Czech Republic (Grant No. 203/97/0033) and the Ministry of Education, Science and Sport of Slovenia (Grant No. PO-0503-103) supported this study. We thank Drs. Bogdan Kralj and Dušan Žigon (Mass Spectrometry Center, Jožef Stefan Institute, Ljubljana, Slovenia) for mass spectral measurements. We are also indebted to Mrs. Hana Geržová (Faculty of Technology, Tomas Bata University in Zlín, Czech Republic) for technical help.
utb.fulltext.projects	203/97/0033
utb.fulltext.projects	PO-0503-103
utb.fulltext.faculty	Faculty of Technology
utb.fulltext.faculty	Faculty of Technology
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