1305317-31-0Relevant articles and documents
From quinoxaline, pyrido[2,3-b]pyrazine and pyrido[3,4-b]pyrazine to pyrazino-fused carbazoles and carbolines
Lassagne, Frédéric,Langlais, Timothy,Caytan, Elsa,Limanton, Emmanuelle,Paquin, Ludovic,Boullard, Manon,Courtel, Coline,Curbet, Idriss,Gédéon, Clément,Lebreton, Julien,Picot, Laurent,Thiéry, Valérie,Souab, Mohamed,Baratte, Blandine,Ruchaud, Sandrine,Bach, Stéphane,Roisnel, Thierry,Mongin, Florence
, (2018)
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).