and not in less polar solvents (entry 6, 7, 8 and 9 in Table ), perhaps due to lower solubility of the reaction components in less polar aprotic solvents. Interestingly, Py-N-ene was formed in the solvents that are also known nucleophiles in addition to their use as solvents for reaction mixtures. Specifically, the dual role of DMSO, as a nucleophile and a base, has been known in addition to its use as solvent. Importantly, this observation indicates why acetonitrile (MeCN) with fairly high polarity does not result in the formation of Py-N-ene (entry 5 in Table ). Furthermore, Py-N-ene has low reaction yields for the reactions in dimethyl formamide (DMF) and dimethyl acetamide (DMA) compared to DMSO. This indicates undesirable nucleophilic-electrophilic interactions between NaH and DMF or DMA, and highlights the role of NaH/DMSO to form Py-N-ene.