Organic letters

TMP–Magnesium and TMP–Zinc Bases for the regioselective metalation of the cinnoline scaffold

T Klatt, DS Roman, T León, P Knochel

Index: Klatt, Thomas; Roman, Daniela Sustac; Leon, Thierry; Knochel, Paul Organic Letters, 2014 , vol. 16, # 4 p. 1232 - 1235

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Citation Number: 18

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 BF3· Et2O and TMP2Mg· 2LiCl or the in situ generated base TMP2Zn· 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 ...