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

MOHAMED, Walid Fathalla, Jaromír MAREK and Pavel PAZDERA. 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. In Proceedings of ECSOC-5, The Fifth International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ecsoc-5.htm. 1st ed. Basel: MDPI, Basel, Switzerland, 2001, p. [a0048], 1 pp. ISBN 3-906980-06-5.

Basic information

• Original name: 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: MOHAMED, Walid Fathalla, Jaromír MAREK and Pavel PAZDERA.
• Edition: 1. vyd. Basel, Proceedings of ECSOC-5, The Fifth International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ecsoc-5.htm, p. [a0048], 1 pp. 2001.
• Publisher: MDPI, Basel, Switzerland

Other information

• Original language: English
• Type of outcome: Proceedings paper
• Field of Study: 10401 Organic chemistry
• Country of publisher: Switzerland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• RIV identification code: RIV/00216224:14310/01:00005301
• Organization unit: Faculty of Science
• ISBN: 3-906980-06-5
• Keywords in English: 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
• Tags: 1, 3-oxathioles, 3-thiazoles, 4-dihydroquinazolin-4-ylidene)thiourea, 5-diyl)-N1-(2-phenyl-3, domino-reactions, N3, N3-(3-oxapentan-1, quinazolines, thioureas

Abstract

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.

Links

• GA203/01/1333, research and development project: Name: Chalkogenorganické sloučeniny - příprava, transformace a strukturní studie

Investor: Czech Science Foundation, Chalcogen organic compounds - synthesis, transformation and structure elucidation

• MSM 143100011, plan (intention): Name: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministry of Education, Youth and Sports of the CR, Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles