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 a Pavel PAZDERA

Základní údaje

Originální název

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

Autoři

MOHAMED, Walid Fathalla, Jaromír MAREK a Pavel PAZDERA

Vydání

1. vyd. Basel, Proceedings of ECSOC-5, The Fifth International Electronic Conference on Synthetic Organic Chemistry, http://www.mdpi.org/ecsoc-5.htm, od s. [a0048], 1 s. 2001

Nakladatel

MDPI, Basel, Switzerland

Další údaje

Jazyk

angličtina

Typ výsledku

Stať ve sborníku

Obor

10401 Organic chemistry

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Kód RIV

RIV/00216224:14310/01:00005301

Organizační jednotka

Přírodovědecká fakulta

ISBN

3-906980-06-5

Klíčová slova anglicky

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

Štítky

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

Změněno: 15. 1. 2002 11:45, doc. RNDr. Pavel Pazdera, CSc.

Anotace

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.

Návaznosti

GA203/01/1333, projekt VaV

Název: Chalkogenorganické sloučeniny - příprava, transformace a strukturní studie

Investor: Grantová agentura ČR, Chalkogenorganické sloučeniny - příprava, transformace a strukturní studie

MSM 143100011, záměr

Název: Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Struktura a vazebné poměry, vlastnosti a analýza syntetických a přírodních molekulových ansamblů

Citovat

MOHAMED, Walid Fathalla, Jaromír MAREK a 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. 1. vyd. Basel: MDPI, Basel, Switzerland, 2001, s. [a0048], 1 s. 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 a 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}. 1. vyd. Basel: MDPI, Basel, Switzerland, 2001, s.~[a0048], 1 s. ISBN~3-906980-06-5.

Podrobný výpis o publikaci