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

Result code in 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>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

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

Original language 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)vi

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/VS96021" target="_blank" >VS96021: Centrum for Analytical Chemistry of Molecular Structure</a><br>

Continuities

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

Publication year

2000

Confidentiality

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

Name of the periodical

Journal of Heterocyclic Chemistry

ISSN

0022-152X

e-ISSN

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Volume of the periodical

37

Issue of the periodical within the volume

4

Country of publishing house

XX - stateless person

Number of pages

7

Pages from-to

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UT code for WoS article

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EID of the result in the Scopus database

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