27151-60-6Relevant academic research and scientific papers
Origins of regioselectivity in the reactions of α-lactams with nucleophiles. Two distinct acid-catalyzed pathways involving O- and N-protonation
Hoffman, Robert V.,Zhao, Zhiqiang,Costales, Abran,Clarke, David
, p. 5284 - 5294 (2002)
Sterically stabilized α-lactams react by two distinct acid-catalyzed pathways. Protonation on oxygen results in nucleophilic attack at the acyl carbon and gives C-2 products. Protonation on nitrogen leads to nucleophilic attack at the C-3 carbon and yield
Rhodium-catalyzed coupling of α-lactams with indole derivatives
Box, Hannah K.,Upul Kumarasinghe,Nareddy, Radhika R.,Akurathi, Gopalakrishna,Chakraborty, Amarraj,Raji, Babatunde,Rowland, Gerald B.
, p. 9709 - 9717 (2015/02/02)
We report herein a method that allows for the formation of a C-N bond between the C-3 carbon of α-lactams and the nitrogen atom of indoles. A general procedure for the coupling of indoles and α-lactams in only 25 min with high yield is reported. The scope of the reaction was extended by the development of a method for the in situ generation of less stable phenyl-substituted α-lactams. The developed method provides an atom-economical method for the formation of substituted α-amino amides that are found in a variety of biologically-active compounds.
Reactions of 1-tert-Butyl-3-phenylaziridinone and α-Bromo-N-tert-butylphenylacetamide with Benzyl-Grignard Reagents
Baumgarten, Henry E.,Chiang, Nein-Chu Robert,Elia, Victor J.,Beum, Paul V.
, p. 5507 - 5512 (2007/10/02)
1-tert-Butyl-3-phenylaziridinone (1) reacts with benzyl halide Grignard reagents (Br and Cl) to give N-tert-butyl-2,3-diphenylpropanamide (4), N-tert-butyl-2-phenylacetamide (3), N-tert-butyl-2-o-tolyl-2-phenylacetamide (5), 1-(tert-butylamino)-1,3-diphenylpropan-2-one (7), N-benzyl-N-tert-butyl-2-phenylacetamide (6), and N-tert-butyl-2-halo-2-phenylacetamide (2, X = Br, Cl).The choice of solvent appears to determine the relative amounts of products 4 and 5.The bromo amide 2 reacts with the Grignard reagent to give 3, 4, 5, 6, and 7 and may be involved to some extentin the reaction of 1 with benzyl-Grignard reagents.The formation of 5 represents anew type of "abnormal" product from a reaction of the benzyl-Grignard reagent; however, this product appears to fit well into the mechanistic pattern established for prior examples.
