About: Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile     Goto   Sponge   NotDistinct   Permalink

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  • 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 or Sandmeyer 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, was cyclized,
  • 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 or Sandmeyer 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, was cyclized, (en)
  • 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. (cs)
Title
  • Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile
  • Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile (en)
  • Vícejaderné heterocykly s kyselou NH skupinou VII. Syntéza některých vícejaderných heterocyklických sloučenin odvozených od 5-fenyl-6-azauracilu. (cs)
skos:prefLabel
  • Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile
  • Polycyclic Heterocycles with Acidic N-H Group VII. Synthesis of some polynuclear heterocyclic compounds derived from 5-phenyl-6-azauracile (en)
  • Vícejaderné heterocykly s kyselou NH skupinou VII. Syntéza některých vícejaderných heterocyklických sloučenin odvozených od 5-fenyl-6-azauracilu. (cs)
skos:notation
  • RIV/61989592:15310/06:00003254!RIV07-MSM-15310___
http://linked.open.../vavai/riv/strany
  • 819-822
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • Z(MSM6198959216)
http://linked.open...iv/cisloPeriodika
  • 5
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 492820
http://linked.open...ai/riv/idVysledku
  • RIV/61989592:15310/06:00003254
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • heterocyclic N-H acids; polynuclear 6-azauracils; substituted 1; 2-dihydro-quinoxalin-2-ones; [1; 2; 4]triazines (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [711303450D66]
http://linked.open...i/riv/nazevZdroje
  • Arkivoc
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • NA
http://linked.open...iv/tvurceVysledku
  • Hlaváč, Jan
  • Buchtík, Roman
  • Slouka, Jan
http://linked.open...n/vavai/riv/zamer
issn
  • 1424-6376
number of pages
http://localhost/t...ganizacniJednotka
  • 15310
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