Synthesis of pyrido [1, 2-a] benzimidazoles by photo-stimulated C–N bond formation via SRN1 reactions

SM Barolo, Y Wang, RA Rossi, GD Cuny - Tetrahedron, 2013 - Elsevier
The photo-stimulated cyclization of 2-(2-halophenylamino) pyridines in liquid ammonia
afforded pyrido [1, 2-a] benzimidazoles via SRN1 mediated C–N bond forming reactions in
moderate to excellent yields (58–94%). This general synthetic strategy was also extended to
a 2-(2-bromophenylamino) pyrazine to give pyrazino [1, 2-a] benzimidazole. Attempts to
employ this reaction using N-(2-chlorophenyl)-3-isoquinolinamine, however, resulted in C–
C bond formation generating 7H-indolo [2, 3-c] isoquinoline.
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