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

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

Frédéric Lassagne, Timothy Langlais, Elsa Caytan, Emmanuelle Limanton, Ludovic Paquin, Manon Boullard, Coline Courtel, Idriss Curbet, Clément Gédéon, Julien Lebreton, Laurent Picot, Valérie Thiéry, Mohamed Souab, etc.

Molecules. 2018 Nov 13;23(11):2961.

PMID: 30428591

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-iodo- quinoxaline, 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).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP290379	Pyrazine		290-37-9	Price

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