From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines - Archive ouverte HAL Access content directly
Journal Articles Molecules Year : 2018

From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines

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Timothy Langlais
  • Function : Author
  • PersonId : 1192540
Elsa Caytan
Emmanuelle Limanton
  • Function : Author
  • PersonId : 1192541
Ludovic Paquin
  • Function : Author
  • PersonId : 1192542
Manon Boullard
  • Function : Author
  • PersonId : 1192543
Coline Courtel
  • Function : Author
  • PersonId : 1192544
Idriss Curbet
  • Function : Author
  • PersonId : 1192545
Clément Gédéon
  • Function : Author
  • PersonId : 1192546
Julien Lebreton
  • Function : Author
  • PersonId : 1192547
Florence Mongin

Abstract

2,3-Diphenylated quinoxaline, pyrido[2,3-b]pyrazine and 8-bromopyrido[3,4-b]pyrazine were halogenated in deprotometalation-trapping reactions using mixed 2,2,6,6-tetramethyl piperidino-based lithium-zinc combinations in tetrahydrofuran. The 2,3-diphenylated 5-iodoquinoxaline, 8-iodopyrido[2,3-b]pyrazine and 8-bromo-7-iodopyrido[3,4-b]pyrazine thus obtained were subjected to palladium-catalyzed couplings with arylboronic acids or anilines, and possible subsequent cyclizations to afford the corresponding pyrazino[2,3-a]carbazole, pyrazino[2 ,3 :5,6] pyrido[4,3-b]indole and pyrazino[2 ,3 :4,5]pyrido[2,3-d]indole, respectively. 8-Iodopyrido[2,3-b] pyrazine was subjected either to a copper-catalyzed C-N bond formation with azoles, or to direct substitution to introduce alkylamino, benzylamino, hydrazine and aryloxy groups at the 8 position. The 8-hydrazino product was converted into aryl hydrazones. Most of the compounds were evaluated for their biological properties (antiproliferative activity in A2058 melanoma cells and disease-relevant kinase inhibition).
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hal-03867783 , version 1 (23-11-2022)

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Frédéric Lassagne, Timothy Langlais, Elsa Caytan, Emmanuelle Limanton, Ludovic Paquin, et al.. From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines. Molecules, 2018, 23 (11), pp.2961. ⟨10.3390/molecules23112961⟩. ⟨hal-03867783⟩
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