The Reactivity Study on N3,N3-(3-Oxapentan-1,5-diyl)-N1-(2-phenyl-3,4-dihydroquinazolin-4-yliden)thiourea. Part 2: Reaction with Phenacyl Bromides and Chloroacetic Acid Derivatives
| Authors | |
|---|---|
| Year of publication | 2001 |
| Type | Article in Proceedings |
| Conference | Proceedings of ECSOC-5, The Fifth International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ecsoc-5.htm |
| MU Faculty or unit | |
| Citation | |
| Web | http://www.mdpi.org/ecsoc-5.htm |
| Field | Organic chemistry |
| Keywords | Quinazolines; thioureas; domino-reactions; N3;N3-(3-oxapentan-1;5-diyl)-N1-(2-phenyl-3;4-dihydroquinazolin-4-ylidene)thiourea; 1;3-oxathioles; 1;3-thiazoles |
| Description | The model N3,N3-(3-oxapentan-1,5-diyl)-N1-(2-phenyl-3,4-dihydro-quinazolin-4-yliden)thiourea 1 reacts with phenacyl bromides to afford N4-(5-aryl-1,3-oxathiol-2-yliden)-2-phenylquinazolin-4-amines orN4-(4,5-diphenyl-1,3-oxathiol-2-yliden)-2-phenyl-4-aminoquinazoline by a kinetically controlled reversible reaction favoring the enolate reaction intermediate, while the 4-[4-aryl-5-(2-phenylquinazolin-4-yl)-1,3-thiazol-2-yl]morpholine was produced by a thermodynamically controlled reversible reaction favoring the C-anion intermediate. The reaction of 1 with chloroacetic acid derivatives gave 4-substituted-2-morpholino-5-(2-phenyl-quinazolin-4-yl)-1,3-thiazoles as the only reaction pathway. |
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