402750-01-0Relevant academic research and scientific papers
Application of a catalyst-free Domino Mannich/Friedel-Crafts alkylation reaction for the synthesis of novel tetrahydroquinolines of potential antitumor activity
Castillo, Juan-Carlos,Jiménez, Elizabeth,Portilla, Jaime,Insuasty, Braulio,Quiroga, Jairo,Moreno-Fuquen, Rodolfo,Kennedy, Alan R.,Abonia, Rodrigo
, p. 932 - 947 (2018)
A useful and efficient method to construct diversely substituted 1,2,3,4-tetrahydroquinolines in good to excellent yields has been developed through a catalyst-free Domino Mannich and intramolecular Friedel-Crafts alkylation reactions of N-arylamines with
Iron-Catalyzed Reductive Ethylation of Imines with Ethanol
Vayer, Marie,Morcillo, Sara P.,Dupont, Jennifer,Gandon, Vincent,Bour, Christophe
supporting information, p. 3228 - 3232 (2018/03/13)
The borrowing hydrogen strategy has been applied to the ethylation of imines with an air-stable iron complex as precatalyst. This approach opens new perspectives in this area as it enables the synthesis of unsymmetric tertiary amines from readily available substrates and ethanol as a C2 building block. A variety of imines bearing electron-rich aryl or alkyl groups at the nitrogen atom could be efficiently reductively alkylated without the need for molecular hydrogen. The mechanism of this reaction, which shows complete selectivity for ethanol over other alcohols, has been studied experimentally and by means of DFT computations.
Robust cyclometallated Ir(iii) catalysts for the homogeneous hydrogenation of N-heterocycles under mild conditions
Wu, Jianjun,Barnard, Jonathan H.,Zhang, Yi,Talwar, Dinesh,Robertson, Craig M.,Xiao, Jianliang
supporting information, p. 7052 - 7054 (2013/09/02)
Cyclometallated Cp*Ir(N∧C)Cl complexes derived from N-aryl ketimines are highly active catalysts for the reduction of N-heterocycles under ambient conditions and 1 atm H2 pressure. The reaction tolerates a broad range of other potentially reducible functionalities and does not require the use of specialised equipment, additives or purified solvent.
Eco-friendly synthesis of imines by ultrasound irradiation
Guzen, Karla P.,Guarezemini, Alexandre S.,órf?o, Aline T.G.,Cella, Rodrigo,Pereira, Claudio M.P.,Stefani, Hélio A.
, p. 1845 - 1848 (2008/02/05)
A series of imines was synthesized by an ultrasound-assisted reaction of aldehydes and primary amines using silica as the promoter. Products were obtained in high yields even in large scale synthesis.
Attempted synthesis of 2-azetidinones via ester enolate condensation reactions with imines and thioimidates
Sharma,Saluja, Aarti,Bhaduri, Susmita,Kanwar, Seema
, p. 1964 - 1969 (2007/10/03)
Reaction of the imines 1 and ethyl isobutyrate in the presence of LDA yields β-lactams 2, whereas thioimidate 4 with the same enolate gives the substituted products 5. When phosphorous containing heterocyclic compound 9 is treated with the enolate of ethyl isobutyrate, a mixture of substituted products 10 and 11 is produced. Mechanistic details of these reactions are described.
On the additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines
Zucca, Cristina,Bravo, Pierfrancesco,Corradi, Eleonora,Meille, Stefano V.,Volonterio, Alessandro,Zanda, Matteo
, p. 424 - 432 (2007/10/03)
The results presented in this paper confirm that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) depends on: (a) the reaction conditions used and (b) the electronic properties of the arylidene moiety on the starting imine. In particular, we show that under kinetic control (-70 °C) the additions involving electron-rich N-arylidene groups occur with very high stereocontrol in favor of the (2S,RS)-diastereomers, whereas an electron-deficient group favors the opposite stereochemical outcome. Based on the observations above, a mechanistic hypothesis is proposed.
