Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F06%3A00003254" target="_blank" >RIV/61989592:15310/06:00003254 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Alternative languages
Result language
angličtina
Original language name
Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile
Original language description
Diazonium salt 2 obtained by diazotation of 3-[3-(6-azauracil-5-yl)-2-aminophenyl]-1,2-dihydro-quinoxalin-3-one 12 was used as a starting compound for the preparation of corresponding 2-hydroxy, 2-chloro, 2-bromo, and 2-iodo derivatives 4-7 using SN1 orSandmeyer reaction. The diazonium salt 2 was converted by reductive cleavage to 3-[3-(6-azauracil-5-yl)phenyl]-1,2-dihydro-quinoxalin-2-one 3 and its coupling with malondinitrile or ethyl cyanoacetylcarbamate gave corresponding hydrazones 9 or 10. Hydrazone 9 was converted to 4-arylazo-3,5-diaminopyrazole 11 via cyclization with hydrazine, and hydrazone 10 was cyclized to 1-[2-(6-azauracil-5-yl)-6-(3,4-dihydro-3-oxo-quinoxalin-2-yl)phenyl]-6-azauracil-5-carbonitrile 12. The slow decomposition of diazonium salt 2 led to benzofuro- derivative 13 that was also found as an undesired side product of all the above mentioned SN1 reactions. Hydrazino derivative 8, which is an intermediate of diazonium salt 2 reduction or hydrazone 10 hydrolysis
Czech name
Vícejaderné heterocykly s kyselou NH skupinou VII. Syntéza některých vícejaderných heterocyklických sloučenin odvozených od 5-fenyl-6-azauracilu.
Czech description
Práce se zabývá studiem reaktivity diazoniové soli vzniklé z 3-[3-(6-azauracil-5-yl)-2-aminophenyl]-1,2-dihydro-quinoxalin-3-onu a využitím této soli k syntéze nejrůznějších substitučních analog.
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2006
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Arkivoc
ISSN
1424-6376
e-ISSN
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Volume of the periodical
NA
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
4
Pages from-to
819-822
UT code for WoS article
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EID of the result in the Scopus database
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