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

D 2001

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

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

Language

English

Type of outcome

Stať ve sborníku

Field of Study

10401 Organic chemistry

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

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

Abstract

V originále

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

Citovat

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.

@inproceedings{388973,
   author = {Mohamed, Walid Fathalla and Marek, Jaromír and Pazdera, Pavel},
   address = {Basel},
   booktitle = {Proceedings of ECSOC-5, The Fifth International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ecsoc-5.htm},
   edition = {1.},
   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},
   language = {eng},
   location = {Basel},
   isbn = {3-906980-06-5},
   pages = {[a0048]},
   publisher = {MDPI, Basel, Switzerland},
   title = {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},
   url = {http://www.mdpi.org/ecsoc-5.htm},
   year = {2001}
}

TY  - JOUR
ID  - 388973
AU  - Mohamed, Walid Fathalla - Marek, Jaromír - Pazdera, Pavel
PY  - 2001
TI  - 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
PB  - MDPI, Basel, Switzerland
CY  - Basel
SN  - 3906980065
KW  - Quinazolines
KW  - thioureas
KW  - domino-reactions
KW  - N3;N3-(3-oxapentan-1;5-diyl)-N1-(2-phenyl-3;4-dihydroquinazolin-4-ylidene)thiourea
KW  - 1;3-oxathioles
KW  - 1;3-thiazoles
UR  - http://www.mdpi.org/ecsoc-5.htm
N2  - 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.
ER  -

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 \textit{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.

Detailed Information on Publication Record