Nitriles are found in many useful compounds. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons. 105-34-0, formula is C4H5NO2, Name is Methyl 2-cyanoacetate. Nitriles are found in many useful compounds. One of the most common occurrences of nitriles is in Nitrile rubber. SDS of cas: 105-34-0.
Wang, Chang-Sheng;Sun, Qiao;Garcia, Felipe;Wang, Chen;Yoshikai, Naohiko research published 《 Cobalt-catalyzed intermolecular [2 + 2 + 2] cycloaddition of nitriles and alkynes: facile synthesis of polyarylpyridines and their mechanochemical cyclodehydrogenation to nitrogen-containing polyaromatics》, the research content is summarized as follows. The transition-metal-catalyzed [2+2+2] cycloaddition of nitriles and alkynes is an established synthetic approach to pyridines; however, these cycloadditions often rely on the use of tethered diynes or cyanoalkynes as one of the reactants. Thus, examples of efficient, fully intermol. catalytic [2+2+2] pyridine synthesis, especially those employing unactivated nitriles and internal alkynes leading to pentasubstituted pyridines, remain scarce. Herein, we report on simple and inexpensive catalytic systems based on cobalt(II) iodide, 1,3-bis(diphenylphosphino)propane, and Zn that promote [2+2+2] cycloaddition of various nitriles and diarylacetylenes for the synthesis of a broad range of polyarylated pyridines. DFT studies support a reaction pathway involving oxidative coupling of two alkynes, insertion of the nitrile into a cobaltacyclopentadiene, and C-N reductive elimination. The resulting tetra- and pentaarylpyridines serve as precursors to hitherto unprecedented nitrogen-containing polycyclic aromatic hydrocarbons via mechanochem. assisted multifold reductive cyclodehydrogenation. Transition metal-catalyzed [2 + 2 + 2] cycloaddition of nitriles and alkynes has been extensively developed as a straightforward and atom-economical synthetic approach to pyridines over the last several decades using various transition metal catalysts, both precious and non-precious. Despite this long history, cycloadditions of this type have often relied on the use of tethered diyne or cyanoalkyne as one of the reactants. Thus, examples of efficient, fully intermol. catalytic [2 + 2 + 2] pyridine synthesis, especially those employing unactivated nitriles and internal alkynes leading to pentasubstituted pyridines, remain scarce. Herein, we report on simple and inexpensive catalytic systems based on cobalt(II) iodide, 1,3-bis(diphenylphosphino)propane, and Zn that promote [2 + 2 + 2] cycloaddition of various nitriles and diarylacetylenes without using a large excess of the nitrile. The present systems allow for the synthesis of broad range of polyarylated pyridines, many of which have not been previously accessed by the [2 + 2 + 2] manifold. Computational studies have supported a reaction pathway involving oxidative coupling of two alkynes, insertion of the nitrile into cobaltacyclopentadiene, and C-N reductive elimination, while shedding light on stepwise nature of the oxidative coupling and insertion processes. We also demonstrate that tetra- and pentaarylpyridines can serve as precursors to hitherto unprecedented nitrogen-containing polycyclic aromatic hydrocarbons via mechanochem. assisted multifold reductive cyclodehydrogenation.
105-34-0, Methyl cyanoacetate is an alkyl cyanoacetate ester.
Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture. It undergoes calcite or fluorite catalyzed Knövenagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α -cyanocinnamic esters.
Methyl Cyanoacetate is often used as a nucleophile in the electrochemical oxidation of catechols. Methyl Cyanoacetate is also a reagent in the synthesis of Methyl 2-Amino-4-trifluoromethylthiophene-3-carboxylate (M287290); a compound used in the synthesis of DPP-IV inhibitors for treating type 2 diabetes., SDS of cas: 105-34-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts