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Fischer indolisation of N-(α-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study

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dc.title Fischer indolisation of N-(α-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study en
dc.contributor.author Proisl, Karel
dc.contributor.author Kafka, Stanislav
dc.contributor.author Urankar, Damijana
dc.contributor.author Gazvoda, Martin
dc.contributor.author Kimmel, Roman
dc.contributor.author Košmrlj, Janez
dc.relation.ispartof Organic and Biomolecular Chemistry
dc.identifier.issn 1477-0520 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2014
utb.relation.volume 12
utb.relation.issue 47
dc.citation.spage 9650
dc.citation.epage 9664
dc.type article
dc.language.iso en
dc.publisher Royal Society of Chemistry (RSC)
dc.identifier.doi 10.1039/c4ob01714e
dc.relation.uri http://pubs.rsc.org/en/Content/ArticleLanding/2014/OB/C4OB01714E#!divAbstract
dc.description.abstract N-(α-ketoacyl)anthranilic acids reacted with phenylhydrazinium chloride in boiling acetic acid to afford 2-(indol-2-carboxamido)benzoic acids in good to excellent yields and 2-indolyl-3,1-benzoxazin-4-ones as by-products. The formation of the latter products could easily be suppressed by a hydrolytic workup. Alternatively, by increasing the reaction temperature and/or time, 2-indolyl-3,1-benzoxazin-4-ones can be obtained exclusively. Optimisations of the reaction conditions as well as the scope and the course of the transformations were investigated. The products were characterized by 1H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H-1H gs-COSY, 1H-13C gs-HSQC, 1H-13C gs-HMBC) with 1H-15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1003927
utb.identifier.obdid 43872178
utb.identifier.scopus 2-s2.0-84910012927
utb.identifier.wok 000345066100021
utb.identifier.coden OBCRA
utb.source j-scopus
dc.date.accessioned 2015-01-13T09:25:43Z
dc.date.available 2015-01-13T09:25:43Z
dc.description.sponsorship TBU in Zlin [IGA/FT/2014/010]; Ministry of Education, Science and Sport, Republic of Slovenia; Slovenian Research Agency [P1-0230, 430-168/2013/114]; EN-FIST Centre of Excellence, Ljubljana
dc.rights Attribution-NonCommercial-NoDerivs 4.0 Unported
dc.rights.uri http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.access openAccess
utb.contributor.internalauthor Proisl, Karel
utb.contributor.internalauthor Kafka, Stanislav
utb.contributor.internalauthor Kimmel, Roman
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