An Aza-Diels–Alder Approach to Crowded Benzoquinolines

Graphene nanoribbons
(GNRs) are promising candidate materials for
the next generation of nanoscale electronics. Described herein is
the synthesis of 2,4,6-substituted benzoquinolines, which constitute
building blocks for nitrogen-doped GNRs. The presented facile and
modular aza-Diels–Alder chemistry accommodates the installation
of diverse functionalities at the crowded benzoquinolines’
2 positions. Given the general utility of the benzoquinoline motif,
these findings hold relevance not only for carbon-based electronics
but also for a range of chemical disciplines.