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@article{484309,
author = {Fathalla, Walid and Marek, Jaromír and Pazdera, Pavel},
article_location = {USA},
article_number = {39},
keywords = {quinazolines; 1;3-thiazoles; 1;3-oxathioles; domino-reactions},
language = {eng},
issn = {0022-152X},
journal = {Journal of Heterocyclic Chemistry},
title = {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},
volume = {2002},
year = {2002}
}
TY - JOUR
ID - 484309
AU - Fathalla, Walid - Marek, Jaromír - Pazdera, Pavel
PY - 2002
TI - 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
JF - Journal of Heterocyclic Chemistry
VL - 2002
IS - 39
SP - 1139
EP - 1139
PB - HeteroCorporation
SN - 0022152X
KW - quinazolines
KW - 1;3-thiazoles
KW - 1;3-oxathioles
KW - domino-reactions
N2 - 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).
ER -
FATHALLA, Walid, Jaromír MAREK and Pavel PAZDERA. 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. \textit{Journal of Heterocyclic Chemistry}. USA: HeteroCorporation, 2002, vol.~2002, No~39, p.~1139-1144. ISSN~0022-152X.
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