Informace o publikaci
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 | |
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Rok publikování | 2008 |
Druh | Článek v odborném periodiku |
Časopis / Zdroj | Journal of Sulfur Chemistry |
Fakulta / Pracoviště MU | |
Citace | |
www | https://doi.org/10.1080/17415990701759685 |
Doi | http://dx.doi.org/10.1080/17415990701759685 |
Obor | Organická chemie |
Klíčová slova | 1.3-thiazoles; 1.3-oxathioles; thermodynamically controlled and kinetically controlled reactions; domino reactions; NK-3R antagonists; 4-heteroaryl-2-phenyl-quinazolines |
Popis | 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. |
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