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Two C═C Bond Participation in Annulation to Pyridines Based on DMF as the Nonadjacent N and C Atom Donors

Miaodong Su, Haiping Liu, Zhongzhong Cao, Yufeng Liu, Hui Li, Zhiwen Nie, Tonglin Yang, Weiping Luo, Qiang Liu, Can‐Cheng Guo

2021The Journal of Organic Chemistry15 citationsDOI

Abstract

-dimethylformamide (DMF) as the N1 and C4 synthons has been carried out. In this reaction, DMF contributed one N atom and one C atom to two disconnected positions of pyridine ring, with no need for an additional nitrogen source. Two C═C bonds in two molecules of substituted styrenes offered four carbon atoms in the presence of iodine and persulfate. With the optimized conditions in hand, both symmetric and unsymmetric diaryl-substituted pyridines were obtained in useful yields. On the basis of relevant literature and a series of control experimental results, a possible mechanism was proposed in this work, which may demonstrate how DMF provides both N1 and C4 sources.

Topics & Concepts

ChemistryAnnulationSynthonPyridineRing (chemistry)Atom (system on chip)MoleculeDimethylformamideMedicinal chemistryStereochemistryOrganic chemistryCatalysisSolventEmbedded systemComputer scienceCatalytic C–H Functionalization MethodsChemical Synthesis and AnalysisSynthesis and Biological Evaluation