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Iodine‐Promoted Synthesis of Dipyrazolo/Diuracil‐Fused Pyridines and <i>o</i>‐Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4‐Methylazaarenes

Xin‐Ke Zhang, Xiaoyu Miao, Hui‐Ru Jiang, Fei Ge, Jiachen Sun, Rui‐Ying Zhang, Qin Ouyang, Weiyu Fan, Yanping Zhu, Yuanyuan Sun

2021Advanced Synthesis & Catalysis20 citationsDOI

Abstract

Abstract The iodine‐promoted oxidative domino annulation and carbonylation process has been developed for the synthesis of biologically important azaarene‐substituted bis‐pyrazolo[3,4‐ b :4′,3′‐ e ]pyridines (BPPs), diuracilpyridines and o ‐amino diheteroaryl ketones. The domino procedure proceeded with easily available methyl azaarenes, 5‐aminouracils and substituted 5‐aminopyrazoles. This protocol is a simple and metal‐free approach which exhibits high functional group compatibility and broad substrates scope. Moreover, this transformation can be applied for the preparation of dipyrazolo/diuracil‐fused pyridines on a gram scale. magnified image

Topics & Concepts

ChemistryDominoAnnulationIodineFunctional groupCombinatorial chemistryOxidative phosphorylationCarbonylationCascade reactionOxidative cleavageCatalysisOrganic chemistryCarbon monoxideBiochemistryPolymerCatalytic C–H Functionalization MethodsSynthesis and Biological EvaluationSynthesis of heterocyclic compounds
Iodine‐Promoted Synthesis of Dipyrazolo/Diuracil‐Fused Pyridines and <i>o</i>‐Amino Diheteroaryl ketones via Oxidative Domino Annulation of 2/4‐Methylazaarenes | Litcius