84636-53-3Relevant academic research and scientific papers
Access to highly functionalized imidazolones bearing α-amino acid estersviaKOH-promoted annulation of amidines, nitrosoarenes and malonic esters
Gao, Wenchao,Huang, Shuangping,Li, Wenhui,Li, Xing,Lin, Jianying,Xin, Jie,Zhai, Pingan
, p. 6473 - 6477 (2021/08/03)
An efficient approach to obtain highly functionalized imidazolones bearing α-amino acid esters through KOH-mediated one-pot three-component annulation of amidines, nitrosoarenes and malonic esters is reported. This reaction features broad substrate scope,
Nitrone/Imine Selectivity Switch in Base-Catalysed Reaction of Aryl Acetic Acid Esters with Nitrosoarenes: Joint Experimental and Computational Study
Volpe, Chiara,Meninno, Sara,Roselli, Angelo,Mancinelli, Michele,Mazzanti, Andrea,Lattanzi, Alessandra
supporting information, p. 5457 - 5466 (2020/10/12)
Herein we report a mild and diastereoselective access to ketonitrones by reacting easily available aryl acetic acid esters and other active methylene compounds, with nitrosoarenes under catalytic loading of 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) at room temperature. Depending on the substitution pattern and nature of the aryl moiety, a switch toward the formation of imines can be observed. The mechanistic framework is put to scrutiny by experimental and theoretical studies, pointing to the formation of a nitroso aldol intermediate, whose fate toward one of the competing pathways, namely hydride transfer or elimination, would depend upon the NOH/CHα relative acidities. (Figure presented.).
Gold(i)-catalyzed formation of dihydroquinolines and indoles from N-aminophenyl propargyl malonates
Gronnier, Colombe,Odabachian, Yann,Gagosz, Fabien
supporting information; experimental part, p. 218 - 220 (2011/03/19)
The use of [XPhosAu(NCMe)]SbF6 in nitromethane at 100 °C allows the rapid and efficient formation of variously substituted dihydroquinolines, which can be subsequently converted into indoles by a rare photochemical rearrangement.
A [3 + 2] and [4 + 3] cycloaddition approach to N-heterocycles via Pd-catalyzed TMM reactions with imines
Trost, Barry M.,Marrs, Christopher M.
, p. 6636 - 6645 (2007/10/02)
The question of cycloadditions of (trimethylenemethane) palladium complexes to heteroation is probed in the context of pyrrolidine syntheses. Whereas simple imines fail to react, imines possessing an electron-withdrawing group at either the carbon or nitrogen enhance the electrophilicity of the imine sufficiently to make it an excellent accetor. Palladium(0) complexes catalyze cycloadditions of 2-((trimethylsilyl)methyl)allyl esters to N-tosyl- and N-nitroimines. The stronger electron-withdrawing nature of the nitre group permits nitrimines derived from relatively hindered ketones to participate. Conjugated cisoid imines lead to [4 + 3] cycloadditions - a process azepine synthesis. Substituted TMM precursors cycloadd with high regioselectivity. The result. are consistent with a two-step addition process. Some of the simple examples explored to determine the scope and limitations of the process reveal simple syntheses of proline and nicotine analogues. The successful employment of imines as direct acceptors for TMM-PdL2 opens a new chapter on metal-catalyzed cycloadditions.
DERIVATIVES OF IMINOMALONIC ESTER
Prosyanik, A. V.,Fedoseenko, D. V.,Markov, V. I.
, p. 1494 - 1503 (2007/10/02)
The synthesis of (alkylimino)malonic esters was realized by the reaction of alkylamines with mesoxalic or dibromomalonic ester. (Halogenimino)malonic esters were obtained for the first time by the reaction of aminomalonic ester with tert-butyl hypochlorite or sodium hypobromite.A new method was developed for the synthesis of (acylimino)malonic esters by the successive bromination and dehydrobromination of (acylamino)malonic esters.The addition of various nucleophiles (water, amines, formamide) at the C=N bond of (acylimino)malonic esters was studied.
ARYLIMINOMALONIC ESTERS
Markov, V. I.,Prosyanik, A. V.,Fedoseenko, D. V.,Loban', S. V.,Starovoitov, V. V.
, p. 2209 - 2215 (2007/10/02)
The condensation of nitrosobenzene with malonis esters is the best method for the production of dialkyl phenyliminomalonates, whereas the thermolysis of symmetrical and unsymmetrical di(arylamino)malonic esters is a good method for the synthesis of substituted dialkyl aryliminomalonates.
