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

Investor logo

Warning

This publication doesn't include Faculty of Education. It includes Faculty of Science. Official publication website can be found on muni.cz.
Authors

FATHALLA Walid MAREK Jaromír PAZDERA Pavel

Year of publication 2002
Type Article in Periodical
Magazine / Source Journal of Heterocyclic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords quinazolines; 1;3-thiazoles; 1;3-oxathioles; domino-reactions
Description 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).
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.