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Dehydrogenative Synthesis of Quinolines and Quinazolines via Ligand-Free Cobalt-Catalyzed Cyclization of 2-Aminoaryl Alcohols with Ketones or Nitriles

Zhiqiang Hao, Xiaoyu Zhou, Zongwen Ma, Caicai Zhang, Zhangang Han, Jin Lin, Guo‐Liang Lu

2022The Journal of Organic Chemistry59 citationsDOI

Abstract

We present a convenient and efficient protocol to synthesize quinolines and quinazolines in one pot under mild conditions. A variety of substituted quinolines were synthesized in good to excellent yields (up to 97% yield) from the dehydrogenative cyclizations of 2-aminoaryl alcohols and ketones catalyzed by readily available Co(OAc)2·4H2O. This cobalt catalytic system also showed high activity in the reactions of 2-aminobenzyl alcohols with nitriles, affording various quinazoline derivatives (up to 95% yield). The present protocol offers an environmentally benign approach for the synthesis of N-heterocycles by employing an earth-abundant cobalt salt under ligand-free conditions.

Topics & Concepts

CobaltYield (engineering)CatalysisChemistryLigand (biochemistry)Combinatorial chemistrySalt (chemistry)Organic chemistryQuinazolineMedicinal chemistryReceptorMaterials scienceMetallurgyBiochemistryQuinazolinone synthesis and applicationsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization Methods