4916-26-1Relevant academic research and scientific papers
Synthesis of polysubstituted 1,4-dihydropyridines via three-component reaction
Balalaie, Saeed,Baoosi, Leila,Tahoori, Fatemeh,Rominger, Frank,Bijanzadeh, Hamid Reza
, p. 738 - 743 (2013/07/27)
An efficient one-pot synthesis of novel N-substituted 1,4-dihydropyridine derivatives via a threecomponent reaction of primary amines, dialkyl acetylenedicarboxylates, and methyl (arylmethylidene) pyruvates has been reported. The reaction is performed using ZnCl2 (40 mol %) in dichloroethane in good to high yields through a domino Michael/cyclization sequence. Notably, the ready availability of the starting materials, high bond-forming efficiency, good to high yields and the high level of practicability of the reaction and work up make this approach an attractive complementary method for access to Nsubstituted 1,4-dihydropyridines.
Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: An emerging innovation
Choudhary, Garima,Peddinti, Rama Krishna
experimental part, p. 3290 - 3299 (2011/12/16)
A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valua
Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of β-enamino ester and amide substrates with α-amido acrylate derivatives
Beholz, Lars G.,Benovsky, Petr,Ward, Donald L.,Barta, Nancy S.,Stille, John R.
, p. 1033 - 1042 (2007/10/03)
The aza-annulation of β-enamino ester and amide substrates with the mixed anhydride of 2-acetamidoacrylic acid was used for the efficient construction of highly substituted α-acetamido δ-lactam products. With the α-acetamido substituent, lactam functionality, and γ-carboxylate group, these δ-lactam products represent an interesting class of conformationally restricted dipeptide analogs. The framework of this lactam hub is structurally related to that of an α-amino acid coupled with a β-amino acid. When α-amino esters derived from naturally occurring amino acids were used in the enamine formation step, subsequent aza-annulation led to branched peptide surrogates with two C-termini that extended from a common N-terminus. Oxidation of the aza-annulation products resulted in the generation of a planar system with peptide functionality radiating from the 1, 3, and 5 positions of the pyridone hub. Alternatively, pyridone products could be formed directly from the enamino amides by reaction with 2-phenyl-4-(ethoxymethylene)oxazolone. Subsequent hydrolysis of the acetamido and ester substituents of the N-benzylpyridones was selectively performed to access unique β-amino acid products. Formation of the mixed anhydride of this acid, followed by amide bond formation with the ester of an α-amino acid, allowed extension of the peptide chain from the dihydropyridone structure.
Oxidation of Enamine-esters with Lead Tetra-acetate. Part 2. Products from N-Aryl- and N-Benzyl-aminofumarates.
Vernon, John M.,Carr, Richard M.,Sukari, Mohamed A.
, p. 1310 - 1334 (2007/10/02)
Dimethyl anilinofumarate and N-benzylaminofumarate are oxidised by lead tetra-acetate to pyrroline, pyrrolin-2-one and pyrrole derivatives.Some other N-arylaminofumarates give the corresponding oxanilates by autoxidative cleavage.
