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

Two C=C bond participation in annulation to pyridines using N,N-dimethylformamide (DMF) as the Ni 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.

Automated summary

In this study, annulation to pyridines using two C=C bond participation was conducted with DMF as the Ni and C4 synthons, providing a convenient and efficient method for the synthesis of symmetric and unsymmetric diaryl-substituted pyridines in useful yields. Through relevant literature and experimental results, a possible mechanism was proposed to explain how DMF can serve as both N1 and C4 sources in this reaction.