title: Condensation-Driven Assembly of Boron-Containing Bis(Heteroaryl) Motifs Using a Linchpin Approach.
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-a]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.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: Shinya
authors.initials: S
authors.lastname: Adachi
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: Sean K
authors.initials: SK
authors.lastname: Liew
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: C Frank
authors.initials: CF
authors.lastname: Lee
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: Alan
authors.initials: A
authors.lastname: Lough
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: Zhi
authors.initials: Z
authors.lastname: He
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: St Denis
authors.affiliation: Drug Discovery Program, Ontario Institute for Cancer Research, MaRS Centre , 661 University Avenue, Suite 510, Toronto, ON M5G 0A3, Canada.|Leslie Dan Faculty of Pharmacy, University of Toronto , 144 College Street, Toronto, ON M5S 3M2, Canada.
authors.forename: Gennady
authors.initials: G
authors.lastname: Poda
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George St., Toronto, ON M5S 3H6, Canada.
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin