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TMP-magnesium and TMP-Zinc bases for the regioselective metalation of the cinnoline scaffold

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 BF3¡¤Et2O and TMP 2Mg¡¤2LiCl or the in situ generated base TMP 2Zn¡¤2MgCl2¡¤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.

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Reference£º
Cinnoline – Wikipedia,
Cinnoline – an overview | ScienceDirect Topics