TMP–Magnesium and TMP–Zinc Bases for
the Regioselective Metalation of the Cinnoline Scaffold
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Abstract
A regioselective
functionalization of cinnolines in positions 3
and 8 using metalations has been developed. This involves either the
use of a frustrated Lewis pair consisting of BF<sub>3</sub>·Et<sub>2</sub>O and TMP<sub>2</sub>Mg·2LiCl or the in situ generated
base TMP<sub>2</sub>Zn·2MgCl<sub>2</sub>·2LiCl. Successive
metalations allow the preparation of 3,8-disubstituted cinnolines.
Various functionalizations by acylation, allylation, and cross-coupling
reactions with aryl halides or alkenyl iodides were carried out successfully
