28544-42-5Relevant academic research and scientific papers
PHOTOREAKTIONEN DES 3-METHYL-4-PHENYLSYDNONS
Pfoertner, Karl-Heinz,Foricher, Joseph
, p. 653 - 657 (1980)
A procedure for the synthesis of 3-methyl-4-phenylsydnone (1) is given.UV. irradiation of 1 in solution generates the nitrile-imine 4 which reacts with activated C,C double bonds and with heterocumulenes to give five-membered heterocycles.In contrast to the 2H-azirines which photochemically react with the C,O double bond of phenylisocyanate, 4 adds to the C,N double bond of the latter.
Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
supporting information, p. 4703 - 4708 (2019/06/27)
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
Metal-catalyzed copolymerization of imines and CO: A non-amino acid route to polypeptides
Sun, Huailin,Zhang, Jian,Liu, Qiuhua,Yu, Lei,Zhao, Jiangyu
, p. 6068 - 6072 (2008/09/16)
(Chemical Equation Presented) The path less taken: Copolymerization of imines and carbon monoxide has long been highly desirable as a route to synthesize polypeptides, but has been difficult to implement because of the lack of appropriate catalysts. This reaction has now been realized for the first time by using a simple cobalt catalyst (see scheme).
The Chemistry of 5-Oxodihydroisoxales. XI; The Photolysis of 3-Hydroxy-4-phenylisoxazol-5(2H)-ones (Phenyldisic Acids)
Prager, Rolf H.,Smith, Jason A.
, p. 217 - 226 (2007/10/02)
3-Hydroxy-2-methyl-4-phenylisoxazol-5(2H)-one, 3-hydroxy-2,4-diphenylisoxazol-5(2H)-one and phenyldisic acid have been photolysed at 254 nm in hydroxylic solvents.By comparision of the respective products with those obtained from 3-methoxy-4-phenylisoxazo
Synthesis with Chelated Imino Carboxylates: The Influence of Chelate Coligands on Reaction Pathways
Drok, Kitty J.,Harrowfield, Jack M.,McNiven, Scott J.,Sargeson, Alan M.,Skelton, Brian W.,White, Allan H.
, p. 1557 - 1594 (2007/10/02)
Synthesis and X-ray crystallography have been used to explore the chemistry of chelates derived from the imines of pyruvic and phenylpyruvic acids held in a chiral environment on cobalt(III) as 2+ (en = ethane-1,2-diamine) and 2+.The latter complex was obtained by an especially facile dehydration of the corresponding β-phenylserine complex.Significant differences in both stereo- and regio-selectivity were detected in reactions of the two complexes, and, for the reaction of butenone with 2+, a pathway indetectable in previously studied reactions of the tetraammine analogue, and leading to a chelate of 4-methyl-5,6-dihydropyridine-2-carboxylate, was observed to be dominant.Kinetically determined stereospecificity was evident in the addition of ethyl cyanoacetate to 2+, whereas equilibrium control appears to exist in the stereoselective addition of nitromethane to both complexes.Crystal structure determinations on five new complexes have been used to establish these points and other important aspects of the chemical syntheses.A considerable number of new imino and amino acids can be derived through the reactions described, and the synthetic utility of both the tetraamine and bis(ethanediamine) complex ion systems in providing the 'free' organic products has been subjected to preliminary evaluation through the isolation of t-leucine, N-methyl-2-phenylglycine, 2-aminomethylalanine, and some vinylglycine derivatives.
