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From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines. 2018
Frédéric Lassagne, and
Timothy Langlais, and
Elsa Caytan, and
Emmanuelle Limanton, and
Ludovic Paquin, and
Manon Boullard, and
Coline Courtel, and
Idriss Curbet, and
Clément Gédéon, and
Julien Lebreton, and
Laurent Picot, and
Valérie Thiéry, and
Mohamed Souab, and
Blandine Baratte, and
Sandrine Ruchaud, and
Stéphane Bach, and
Thierry Roisnel, and
Florence Mongin
Univ Rennes, CNRS, Institut des Sciences Chimiques de Rennes (ISCR)-UMR 6226, F-35000 Rennes, France. frederic.lassagne@univ-rennes1.fr.
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).
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