In 2019,Journal of the American Chemical Society included an article by Le Fouler, Vincent; Chen, Yu; Gandon, Vincent; Bizet, Vincent; Salome, Christophe; Fessard, Thomas; Liu, Fang; Houk, K. N.; Blanchard, Nicolas. Product Details of 78191-00-1. The article was titled 《Activating Pyrimidines by Pre-distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels-Alder Reactions》. The information in the text is summarized as follows:
Pyrimidines are almost unreactive partners in Diels-Alder cycloadditions with alkenes and alkynes, and only reactions under drastic conditions were previously reported. The authors describe how 2-hydrazonylpyrimidines, easily obtained in two steps from com. available 2-halopyrimidines, can be exceptionally activated by trifluoroacetylation. This allows a Diels-Alder cycloaddition under very mild reaction conditions, leading to a large diversity of aza-indazoles, a ubiquitous scaffold in medicinal chem. This reaction is general and scalable and has an excellent functional group tolerance. A straightforward synthesis of a key intermediate of Bayer’s Vericiguat illustrates the potential of this cycloaddition strategy. Quantum mech. calculations show how the simple N-trifluoroacetylation of 2-hydrazonylpyrimidines distorts the substrate into a transition-state-like geometry that readily undergoes the intramol. Diels-Alder cycloaddition The results came from multiple reactions, including the reaction of N-Methoxy-N-methylacetamide(cas: 78191-00-1Product Details of 78191-00-1)
N-Methoxy-N-methylacetamide(cas: 78191-00-1) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Product Details of 78191-00-1
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics