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

J 2008

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

MOHAMED, Walid Fathalla M., Jaromír MAREK a Pavel PAZDERA

Základní údaje

Originální název

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

Název česky

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

Autoři

MOHAMED, Walid Fathalla M. (818 Egypt), Jaromír MAREK (203 Česká republika, domácí) a Pavel PAZDERA (203 Česká republika, garant, domácí)

Vydání

Journal of Sulfur Chemistry, New York, Taylor & Francis, 2008, 1741-5993

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Kód RIV

RIV/00216224:14310/08:00025408

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1080/17415990701759685

UT WoS

000269194500005

Klíčová slova anglicky

1.3-thiazoles; 1.3-oxathioles; thermodynamically controlled and kinetically controlled reactions; domino reactions; NK-3R antagonists; 4-heteroaryl-2-phenyl-quinazolines

Štítky

1.3-oxathioles, 1.3-thiazoles, 4-heteroaryl-2-phenyl-quinazolines, domino reactions, NK-3R antagonists

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 19. 6. 2020 14:38, Mgr. Marie Šípková, DiS.

Anotace

V originále

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.

Návaznosti

MSM 143100011, záměr

Název: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

2A-1TP1/090, projekt VaV

Název: Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy.

Investor: Ministerstvo průmyslu a obchodu ČR, Nové katalyzátory a činidla pro udržitelné zelené syntézy a kombinatoriální syntézy

Citovat

MOHAMED, Walid Fathalla M., Jaromír MAREK a Pavel PAZDERA. 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. Journal of Sulfur Chemistry. New York: Taylor & Francis, 2008, roč. 29, č. 1, s. 31-42. ISSN 1741-5993. Dostupné z: https://dx.doi.org/10.1080/17415990701759685.

@article{764880,
   author = {Mohamed, Walid Fathalla M. and Marek, Jaromír and Pazdera, Pavel},
   article_location = {New York},
   article_number = {1},
   doi = {http://dx.doi.org/10.1080/17415990701759685},
   keywords = {1.3-thiazoles; 1.3-oxathioles; thermodynamically controlled and kinetically controlled reactions; domino reactions; NK-3R antagonists; 4-heteroaryl-2-phenyl-quinazolines},
   language = {eng},
   issn = {1741-5993},
   journal = {Journal of Sulfur Chemistry},
   title = {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},
   url = {https://doi.org/10.1080/17415990701759685},
   volume = {29},
   year = {2008}
}

TY  - JOUR
ID  - 764880
AU  - Mohamed, Walid Fathalla M. - Marek, Jaromír - Pazdera, Pavel
PY  - 2008
TI  - 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
JF  - Journal of Sulfur Chemistry
VL  - 29
IS  - 1
SP  - 31-42
EP  - 31-42
PB  - Taylor & Francis
SN  - 17415993
KW  - 1.3-thiazoles
KW  - 1.3-oxathioles
KW  - thermodynamically controlled and kinetically controlled reactions
KW  - domino reactions
KW  - NK-3R antagonists
KW  - 4-heteroaryl-2-phenyl-quinazolines
UR  - https://doi.org/10.1080/17415990701759685
L2  - https://doi.org/10.1080/17415990701759685
N2  - 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.
ER  -

MOHAMED, Walid Fathalla M., Jaromír MAREK a Pavel PAZDERA. 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. \textit{Journal of Sulfur Chemistry}. New York: Taylor \&{} Francis, 2008, roč.~29, č.~1, s.~31-42. ISSN~1741-5993. Dostupné z: https://dx.doi.org/10.1080/17415990701759685.

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