Rhodium-catalyzed C–H activation/annulation of amidines with 4-diazoisochroman-3-imines toward isochromeno[3,4-c]isoquinolines?

Organic & Biomolecular Chemistry Pub Date: 2019-08-30 DOI: 10.1039/C9OB01612K

Abstract

A rhodium-catalyzed C–H activation/annulation of amidines with 4-diazoisochroman-3-imines has been established to afford a series of 8-amino-5H-isochromeno[3,4-c]isoquinolines in moderate to good yields with good functional group tolerance. This reaction proceeded in a sequential C–H activation/carbene migration insertion/intramolecular annulation procedure and featured the construction of a C–C and C–N bond in one pot. UV-vis and fluorescence spectral analyses of these highly fused heteroarenes were performed.

Graphical abstract: Rhodium-catalyzed C–H activation/annulation of amidines with 4-diazoisochroman-3-imines toward isochromeno[3,4-c]isoquinolines
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