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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F00%3A00000987" target="_blank" >RIV/61989592:15310/00:00000987 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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)vi

Název v anglickém jazyce

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

Popis výsledku anglicky

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)vi

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/VS96021" target="_blank" >VS96021: Centrum analytické chemie molekulárních struktur</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2000

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Heterocyclic Chemistry

ISSN

0022-152X

e-ISSN

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Svazek periodika

37

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

XX - osoby bez státní příslušnosti

Počet stran výsledku

7

Strana od-do

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Kód UT WoS článku

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EID výsledku v databázi Scopus

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