Informace o publikaci
New Domino-Reaction for the Synthesis of N4-(5-Aryl-1,3-oxathiol-2-yliden)-2-phenylquinazolin-4-amines and 4-[4-Aryl-5-(2-phenylquinazolin-4-yl)-1,3-thiazol-2-yl]morpholine
| Autoři | |
|---|---|
| Rok publikování | 2002 |
| Druh | Článek v odborném periodiku |
| Časopis / Zdroj | Journal of Heterocyclic Chemistry |
| Fakulta / Pracoviště MU | |
| Citace | |
| Obor | Organická chemie |
| Klíčová slova | quinazolines; 1;3-thiazoles; 1;3-oxathioles; domino-reactions |
| Popis | The model morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide (1) reacts with phenacyl bromides to afford N4-(5-aryl-1,3-oxathiol-2-yliden)-2-phenylquinazolin-4-amines (4) or N4-(4,5-diphenyl-1,3-oxathiol-2-yliden)-2-phenyl-4-aminoquinazoline (5) by a thermodynamically controlled reversible reaction favoring the enolate intermediate, while the 4-[4-aryl-5-(2-phenylquinazolin-4-yl)-1,3-thiazol-2-yl]morpholine (8) was produced by a kinetically controlled reaction favoring the C-anion intermediate. 1H nmr, 13C nmr, ir, mass spectroscopy and x-ray identified compounds (4), (5) and (8). |
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