About: Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation

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About: Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The cyclization of phenacyl anthranilate has been studied with the aim to develop the synthesis of 2-(2'-aminophenyl)-4 phenyloxazole. However, a different course of the reaction than expected was observed. 2-Phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazole (3a) was formed by the reaction of phenacyl anthranilate (2) with ammonium acetate under various conditions. 3-Hydroxy-2-phenyl-4(1H)-quinolinone (4) arose by heating compound 3a in acetic acid. The same compound was obtained by melting compound 3a, but the yield was lower. Different types of Products resulted in the reaction of compound 3a with acetic anhydride. Under mild conditions acetylated products 2-acetoxymethyl-2-phenyl-4-oxo-1,2,3,4 tetrahydroquinazoline (7a) and 2-acetoxymethyl-3-acetyl-2 phenyl-4-oxo- 1,2,3,4-tetrahydroquinazoline (8) were prepared. If the reaction was carried out under reflux of the reaction mixture, molecular rearrangement took place to give cis and trans 2-methyl-4-oxo-3-(1-phenyl-2-acetoxy)vinyl 3,4dihydroqu The cyclization of phenacyl anthranilate has been studied with the aim to develop the synthesis of 2-(2'-aminophenyl)-4 phenyloxazole. However, a different course of the reaction than expected was observed. 2-Phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazole (3a) was formed by the reaction of phenacyl anthranilate (2) with ammonium acetate under various conditions. 3-Hydroxy-2-phenyl-4(1H)-quinolinone (4) arose by heating compound 3a in acetic acid. The same compound was obtained by melting compound 3a, but the yield was lower. Different types of Products resulted in the reaction of compound 3a with acetic anhydride. Under mild conditions acetylated products 2-acetoxymethyl-2-phenyl-4-oxo-1,2,3,4 tetrahydroquinazoline (7a) and 2-acetoxymethyl-3-acetyl-2 phenyl-4-oxo- 1,2,3,4-tetrahydroquinazoline (8) were prepared. If the reaction was carried out under reflux of the reaction mixture, molecular rearrangement took place to give cis and trans 2-methyl-4-oxo-3-(1-phenyl-2-acetoxy)vinyl 3,4dihydroqu (en)
Title	Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation (en)
skos:prefLabel	Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation Preparation of 2-phenyl-2-hydroxymethyl-4-oxo-1,2,3,4 tetrahydroquinazoline and 2-methyl-4-oxo-3,4-dihydroquinazoline derivatives formation (en)
skos:notation	RIV/61989592:15310/00:00000987!RIV/2001/MSM/153101/N
http://linked.open.../vavai/riv/strany	831
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(VS96021), Z(MSM 153100008), Z(MSM 153100013)
http://linked.open...iv/cisloPeriodika	4
http://linked.open...vai/riv/dodaniDat	2001
http://linked.open...aciTvurceVysledku	Hlaváč, Jan Lemr, 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 Palackého v Olomouci / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	722957
http://linked.open...ai/riv/idVysledku	RIV/61989592:15310/00:00000987
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open...ontrolniKodProRIV	[DD8A34A8644D]
http://linked.open...i/riv/nazevZdroje	Journal of Heterocyclic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (xsd:int)
http://linked.open...vavai/riv/projekt	Centrum for Analytical Chemistry of Molecular Structure
http://linked.open...UplatneniVysledku	2000
http://linked.open...v/svazekPeriodika	37
http://linked.open...iv/tvurceVysledku	Hlaváč, Jan Lemr, Karel Hradil, Pavel Kvapil, L. Lyčka, A. Weidlich, T.
http://linked.open...n/vavai/riv/zamer	http://linked.opendata.cz/resource/domain/vavai/zamer/MSM%20153100008 http://linked.opendata.cz/resource/domain/vavai/zamer/MSM%20153100013
issn	0022-152X
number of pages	7 (xsd:int)
http://localhost/t...ganizacniJednotka	15310

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