Quality Control of Methyl 3-methylbenzoate《Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes》 was published in 2019. The authors were van Vliet, Kaj M.;Polak, Lara H.;Siegler, Maxime A.;van der Vlugt, Jarl Ivar;Guerra, Celia Fonseca;de Bruin, Bas, and the article was included in《Journal of the American Chemical Society》. The author mentioned the following in the article:
Direct synthetic routes to amidines are desired, as they are widely present in many biol. active compounds and organometallic complexes. N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper-catalyzed three-component reaction of aryl acetylenes, amines, and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO2 as the only byproduct. Transformation of the dioxazolones on the Cu catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu-C bond rather than undergoing an undesired Curtius rearrangement. For nonaromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 min. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple copper(I) iodide (CuI) as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol %. The herein reported procedure not only provides a new, practical, and direct route to N-acyl amidines but also represents a new type of C-N bond formation. And Methyl 3-methylbenzoate (cas: 99-36-5) was used in the research process.
Methyl 3-methylbenzoate (cas: 99-36-5) is a common ester.Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids.Quality Control of Methyl 3-methylbenzoate Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries.
Reference:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics