A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

Abstract

A rich array of reactions occur using N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMAc) as reactants, these two amides being able to deliver their own H, C, N, and O atoms for the synthesis of a variety of compounds. This account highlights the literature published since June 2018, completing previous reviews by the author.

Electro‐oxidative Methylation of 2‐Isocyanobiaryls Using N,N‐dimethylformamide (DMF) as Carbon Source: Synthesis of 6‐Methylphenanthridines

“…On the basis of the above‐mentioned experimental evidence as well as the existing literature reports, [11b,d–e,13] a plausible reaction mechanism for the alkylation of 2‐isocyanobiaryls was proposed. The methylation reaction of 2‐isocyano‐1,1′‐biphenyl ( 1 a ) with DMF was chosen as representatives as depicted in Scheme 6.…”

“…This experimental observation implied that the reaction should proceed through a radical pathway. As previously described, [3a–b,13] DMF has the capability to function as a C 1 source, deriving either from its formyl group (−CHO) [11] or its methyl group adjacent to the nitrogen atom ( N −CH 3 ) [11b,d–e] . Thus, when DMA was employed in place of DMF, compound 2 a was obtained in modest yield (44 % yield) (Scheme 4d).…”