About: A study of 2-substituted 3,1-benzoxazin-4-ones

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Description	This paper describes our work concerning the preparation of novel benzoxazinones substituted with indole moiety or acyl in position 2. Their preparation is achieved by cyclodehydration of the appropriate N-acylanthranilic acids by means of acetic anhydride or thionyl chloride, which is consistent with the standard procedure. In addition, a new route to starting N-acylanthranilic acids has been established. Firstly, N-(α-ketoacyl)anthranilic acids were readily obtained from 4-hydroxyquinolin-2-ones by two-step oxidation including peracetic acid hydroxylation into the corresponding 3-hydroxyquinoline-2,4-diones and subsequent oxidative ring opening with periodic acid or sodium periodate. In the cases of the preparation of the mentioned indole derivatives, the appropriate transformations of α-ketoacyl chain were carried out by known chemistry. As a part of our continued interest in the reactivity of various heterocyclic systems, we have studied reactions of title compounds with some nucleophiles. All compounds under investigation were characterized by available methods of structural analysis including high resolution mass spectrometry and two-dimensional NMR techniques. This paper describes our work concerning the preparation of novel benzoxazinones substituted with indole moiety or acyl in position 2. Their preparation is achieved by cyclodehydration of the appropriate N-acylanthranilic acids by means of acetic anhydride or thionyl chloride, which is consistent with the standard procedure. In addition, a new route to starting N-acylanthranilic acids has been established. Firstly, N-(α-ketoacyl)anthranilic acids were readily obtained from 4-hydroxyquinolin-2-ones by two-step oxidation including peracetic acid hydroxylation into the corresponding 3-hydroxyquinoline-2,4-diones and subsequent oxidative ring opening with periodic acid or sodium periodate. In the cases of the preparation of the mentioned indole derivatives, the appropriate transformations of α-ketoacyl chain were carried out by known chemistry. As a part of our continued interest in the reactivity of various heterocyclic systems, we have studied reactions of title compounds with some nucleophiles. All compounds under investigation were characterized by available methods of structural analysis including high resolution mass spectrometry and two-dimensional NMR techniques. (en)
Title	A study of 2-substituted 3,1-benzoxazin-4-ones A study of 2-substituted 3,1-benzoxazin-4-ones (en)
skos:prefLabel	A study of 2-substituted 3,1-benzoxazin-4-ones A study of 2-substituted 3,1-benzoxazin-4-ones (en)
skos:notation	RIV/70883521:28110/12:43869044!RIV13-MSM-28110___
http://linked.open...avai/predkladatel	Fakulta technologická
http://linked.open...avai/riv/aktivita	S
http://linked.open...avai/riv/aktivity	S
http://linked.open...iv/cisloPeriodika	106
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Kafka, Stanislav Proisl, Karel
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Tomáše Bati ve Zlíně / Fakulta technologická
http://linked.open...dnocenehoVysledku	120662
http://linked.open...ai/riv/idVysledku	RIV/70883521:28110/12:43869044
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	benzoxazinone, indole, N-acylanthranilic acid, hydroxy quinolinone, hydroxy quinolinedione, oxidative ring opening, periodic acid, periodate (en)
http://linked.open.../riv/klicoveSlovo	N-acylanthranilic acid benzoxazinone hydroxy quinolinedione hydroxy quinolinone indole periodate periodic acid oxidative ring opening
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[4EF84E3A9BF2]
http://linked.open...i/riv/nazevZdroje	Chemické listy
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	2012
http://linked.open...iv/tvurceVysledku	Kafka, Stanislav Proisl, Karel Košmrlj, J. Urankar, D.
issn	0009-2770
number of pages	1 (xsd:int)
http://localhost/t...ganizacniJednotka	28110
is http://linked.open...avai/riv/vysledek of	A study of 2-substituted 3,1-benzoxazin-4-ones

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