About: A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-...

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About: A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-... Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The treatment of 3-acyl-4-hydroxy-1H-quinolin-2-ones (1) with ethyl (triphenylphosphoranylidene)acetate leads to 5,6-dihydro-2H-pyranol[3,2-c]quinoline-2,5-diones (2), which were brominated to 3-bromo derivatives (4). Alkaline hydrolysis of 4 gives 2-alkyl/aryl-4-oxo-4,5-dihydrofuro[3,2-c]quinoline-3-carboxylic acids (6), which were decarboxylated to 2-alkyl/aryl-5H-furo[3,2-c]quinolin-4-ones (8). The reaqction of 3-acyl-4-hydroxy-1-methyl-1H-quinolin-2-one (1a) with ethyl (triphenylphosphoranylidene)chloroacetate proceeds not only at the acetyl but also at the amide group to give a mixture of ethyl 3,5-dimethyl-4-oxo-4,5-dihydrofuro[3,2-c]quinoline-2-carboxylate (11a) and ethyl 4,6-dimethyl-2-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinolin-5-ylidene(chloro)acetate (12a). The reaction mechanism of the molecular rearrangement of 4 to 6 is discussed. The treatment of 3-acyl-4-hydroxy-1H-quinolin-2-ones (1) with ethyl (triphenylphosphoranylidene)acetate leads to 5,6-dihydro-2H-pyranol[3,2-c]quinoline-2,5-diones (2), which were brominated to 3-bromo derivatives (4). Alkaline hydrolysis of 4 gives 2-alkyl/aryl-4-oxo-4,5-dihydrofuro[3,2-c]quinoline-3-carboxylic acids (6), which were decarboxylated to 2-alkyl/aryl-5H-furo[3,2-c]quinolin-4-ones (8). The reaqction of 3-acyl-4-hydroxy-1-methyl-1H-quinolin-2-one (1a) with ethyl (triphenylphosphoranylidene)chloroacetate proceeds not only at the acetyl but also at the amide group to give a mixture of ethyl 3,5-dimethyl-4-oxo-4,5-dihydrofuro[3,2-c]quinoline-2-carboxylate (11a) and ethyl 4,6-dimethyl-2-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinolin-5-ylidene(chloro)acetate (12a). The reaction mechanism of the molecular rearrangement of 4 to 6 is discussed. (en)
Title	A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-... A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-... (en)
skos:prefLabel	A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-... A new synthesis of 4-alkyl/aryl-5,6-dihydro-2H-pyrano[3,2-c]quinoline-2,5-diones and molecular rearrangement of their 3-bromo derivatives to 2-alkyl/aryl-4-oxo-... (en)
skos:notation	RIV/70883521:28110/03:63501410!RIV/2004/MSM/281104/N
http://linked.open.../vavai/riv/strany	799-815
http://linked.open...avai/riv/aktivita	Z
http://linked.open...avai/riv/aktivity	Z(MSM 265200015)
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2004
http://linked.open...aciTvurceVysledku	Kořistek, Kamil Klásek, Antonín
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	597005
http://linked.open...ai/riv/idVysledku	RIV/70883521:28110/03:63501410
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Wittig reaction, molecular rearrangement (en)
http://linked.open.../riv/klicoveSlovo	Wittig reaction molecular rearrangement
http://linked.open...odStatuVydavatele	JP - Japonsko
http://linked.open...ontrolniKodProRIV	[E6CF50E7609D]
http://linked.open...i/riv/nazevZdroje	HETEROCYCLES
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...ocetUcastnikuAkce	0 (xsd:int)
http://linked.open...nichUcastnikuAkce	0 (xsd:int)
http://linked.open...UplatneniVysledku	2003
http://linked.open...v/svazekPeriodika	60
http://linked.open...iv/tvurceVysledku	Halada, Petr Sedmera, Petr Klásek, Antonín Kořistek, Kamil
http://linked.open...n/vavai/riv/zamer	http://linked.opendata.cz/resource/domain/vavai/zamer/MSM%20265200015
issn	0385-5414
number of pages	17 (xsd:int)
http://localhost/t...ganizacniJednotka	28110

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