One-pot domino synthesis of 4-heteroaryl-2-phenyl-quinazolines bearing 5-aryl-l,3-oxathiol-2-ylidene amine and substituted 1,3-thiazole groups

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F08%3A00025408" target="_blank" >RIV/00216224:14310/08:00025408 - 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

One-pot domino synthesis of 4-heteroaryl-2-phenyl-quinazolines bearing 5-aryl-l,3-oxathiol-2-ylidene amine and substituted 1,3-thiazole groups

Original language description

The reaction of thioamides 1-5 with phenacyl halides offers the advantage of an efficient domino synthesis of the title 4-heteroaryl-2-phenylquinazolines bearing 1,3-oxathiol-2-ylidene amine 6a-d and 1,3-thiazoles 7-11. The reaction shows unexpected thermodynamic and kinetic control products. In the same manner, thioamides 1, 2 and 4 react with methyl chloroacetate to afford 4-[2-dialkylamino-4(5//)-oxo-l, 3-thiazol-5-yl]-2-phenyl-quinazolin-4(3//)-ylidene 12,13 and 14, respectively. Similarly, 2-morpholtno-5-(2-phenylquinazolin-4-yl)thiazol-4-amine 15 is formed by the reaction of 1 with chloroacetonitrile. Synthesized compounds were characterized on the basis of the well known reaction mechanisms, elemental analysis, NMR, mass spectroscopy and X-ray data.

Czech name

One-pot domino synthesis of 4-heteroaryl-2-phenyl-quinazolines bearing 5-aryl-l,3-oxathiol-2-ylidene amine and substituted 1,3-thiazole groups

Czech description

The reaction of thioamides 1-5 with phenacyl halides offers the advantage of an efficient domino synthesis of the title 4-heteroaryl-2-phenylquinazolines bearing 1,3-oxathiol-2-ylidene amine 6a-d and 1,3-thiazoles 7-11. The reaction shows unexpected thermodynamic and kinetic control products. In the same manner, thioamides 1, 2 and 4 react with methyl chloroacetate to afford 4-[2-dialkylamino-4(5//)-oxo-l, 3-thiazol-5-yl]-2-phenyl-quinazolin-4(3//)-ylidene 12,13 and 14, respectively. Similarly, 2-morpholtno-5-(2-phenylquinazolin-4-yl)thiazol-4-amine 15 is formed by the reaction of 1 with chloroacetonitrile. Synthesized compounds were characterized on the basis of the well known reaction mechanisms, elemental analysis, NMR, mass spectroscopy and X-ray data.

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/2A-1TP1%2F090" target="_blank" >2A-1TP1/090: New catalysts and reagents for sustainable green syntheses and combinatorial syntheses</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2008

Confidentiality

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

Name of the periodical

Journal ofSulfur Chemistry

ISSN

1741-5993

e-ISSN

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Volume of the periodical

29

Issue of the periodical within the volume

1

Country of publishing house

US - UNITED STATES

Number of pages

12

Pages from-to

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UT code for WoS article

000263917900012

EID of the result in the Scopus database

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