78120-37-3Relevant academic research and scientific papers
Expanding Blaise-Type Reactions towards Indium-Mediated Transformations of α-Bromo-β-keto Esters with Nitriles
Li, Luomo,Babaoglu, Emre,Harms, Klaus,Hilt, Gerhard
, p. 4543 - 4547 (2017)
The aim of this work is the identification of mild reaction conditions for the Blaise-type transformation of brominated β-keto esters with nitriles to generate enamino-substituted keto esters. The best results were obtained when a combination of indium metal (0.7 equiv.) with indium trichloride (1.6 equiv.) were applied at 60 °C for 20 to 72 hours, and these conditions could be applied to a broad range of nitriles and a significant number of different β-keto esters. The transformation of aliphatic nitriles proved to be difficult and gave only moderate yields. However, aromatic nitriles gave good yields in many cases. The applicability range of β-keto esters is acceptable while some electron-deficient aryl-substituents on the keto ester were challenging substrates. Nevertheless, we were able to expand the scope of the Blaise-type reaction towards brominated β-keto esters significantly.
ENAMINE CHEMISTRY, PART XXI. N- AND/OR C-SUBSTITUTION (ALKYLATION, ACYLATION) OF ETHYL 3-AMINO-2-BUTENOATE. THE PREPARATION OF 2-SUBSTITUTED 4-METHYL-1,3-THIAZINE-6-THIONES
Shabana, R.,Rasmussen, J. B.,Lawesson, S.-O.
, p. 75 - 82 (2007/10/02)
Alkylation of ethyl 3-amino-2-butenoate, 1, with methyl iodide, ethyl iodide, and benzyl bromide gave both C- and N-alkylated products (contrary to earlier findings) the ratio of which was determined by GLC.Methylation of 1 was studied under different con
