Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl)
Motifs Using a Linchpin Approach
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Abstract
Herein, we describe
the bromomethyl acyl boronate linchpin–an
enabling reagent for the condensation-driven assembly of novel bis(heteroaryl)
motifs. This building block is readily accessible from commercially
available starting materials. A variety of 2-amino- and 2-methylpyridines
were reacted with MIDA-protected bromomethyl acylboronate to afford
2-boryl imidazo[1,2-<i>a</i>]pyridine and 2-boryl
indolizine derivatives, respectively, in excellent yields. Subsequent
condensation with hydroxyamidines and hydrazonamides converted the
intermediate heterocycles into novel boron-containing bis(heteroaryl)
units characterized by high thermal stability