15286-50-7Relevant academic research and scientific papers
Synthesis of β-Phosphinolactams from Phosphenes and Imines
Fu, Xingyang,Li, Xinyao,Xu, Jiaxi
supporting information, p. 8733 - 8737 (2021/11/17)
Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.
Superacid-promoted synthesis of quinoline derivatives
Klumpp, Douglas A.,Stentzel, Michael R.,Vuong, Hein
supporting information, (2020/01/24)
A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.
Synthesis, Cytotoxicity and Antimicrobial Evaluation of New Coumarin-Tagged β-Lactam Triazole Hybrid
Awolade, Paul,Cele, Nosipho,Dhawan, Sanjeev,Jonnalagadda, Sreekantha B.,Kaur, Mandeep,Kisten, Prishani,Pillay, Ashona-Singh,Saha, SouravTaru,Singh, Parvesh
, (2020/01/24)
A series of coumarin-tagged β-lactam triazole hybrids (10a–10o) were synthesized and tested for their cytotoxic activity against MDA-MB-231 (triple negative breast cancer), MCF-7 (estrogen receptor positive breast cancer (ER+)) and A549 (human lung carcinoma) cancer cell lines including one normal cell line, HEK-293 (human embryonic kidney). Two compounds 10b and 10d exhibited substantial cytotoxic effect against MCF-7 cancer cell lines with IC50 values of 53.55 and 58.62 μm, respectively. More importantly, compounds 10b and 10d were non-cytotoxic against HEK-293 cell lines. Structure–activity relationship (SAR) studies suggested that the nitro and chloro group at the C-3 position of phenyl ring are favorable for anticancer activity, particularly against MCF-7 cell lines. Furthermore, antimicrobial evaluation of these compounds revealed modest inhibition of examined pathogenic strains with compounds 10c and 10i being the most promising antimicrobial agents against Pseudomonas aeruginosa and Candida albicans, respectively.
Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines
Kim, Eunae,Park, Sehoon,Chang, Sukbok
supporting information, p. 5765 - 5769 (2018/03/28)
Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one-pot gram-scale synthesis. Moreover, a diastereoselective introduction of the β-silyl group was also found to be feasible (d.r. up to 71:29).
Insertion of Nitriles into Zirconocene 1-aza-1,3-diene Complexes: Chemoselective Synthesis of N-H and N-Substituted Pyrroles
Yu, Shasha,Xiong, Meijun,Xie, Xin,Liu, Yuanhong
supporting information, p. 11596 - 11599 (2016/02/19)
The direct insertion of nitriles into zirconocene-1-aza-1,3-diene complexes provides an efficient, chemoselective, and controllable synthesis of N-H and N-substituted pyrroles upon acidic aqueous work-up. The outcome of the reaction (that is, the formatio
Solvent-free synthesis, DNA-topoisomerase II activity and molecular docking study of new asymmetrically N,N′-substituted ureas
Andressa, Esteves-Souza,Rodrigues-Santos, Claudio E.,De Nigris Del Cistia, Catarina,Da Silva, Daniel Rosa,Sant'Anna, Carlos Mauricio R.,Echevarria, Aurea
, p. 12882 - 12894 (2013/02/22)
A new series of asymmetrically N,N′-substituted ureas 20-25 was prepared using solvent free conditions, which is an eco-friendly methodology, starting with Schiff bases derived from cinnamaldehyde and p-substituted anilines, which are subsequently submitt
A modular approach to α,β-unsaturated N-aryl ketonitrones
Hood, Tyler S.,Bryan Huehls,Yang, Jiong
supporting information; experimental part, p. 4679 - 4682 (2012/09/05)
A modular approach to α,β-unsaturated N-aryl ketonitrones has been developed. Specifically, condensation of anilines and enals followed by alkylation of the resulting α,β-unsaturated imines provided N-allyl anilines, which were subjected to oxidation with
GREEN SYNTHESIS OF ARYL ALDIMINES USING ETHYL LACTATE
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Page/Page column 4-5, (2011/08/22)
The present invention relates to a method for preparing aryl aldimines. In particular, the present invention relates to methods of preparing aryl aldimines that uses environmentally friendly solvent systems.
Sulfonic acid supported on hydroxyapatite-encapsulated-γ-Fe 2O3 nanocrystallites as a magnetically separable catalyst for one-pot reductive amination of carbonyl compounds
Deng, Jia,Mo, Li-Ping,Zhao, Fei-Yang,Hou, Lan-Lan,Yang, Li,Zhang, Zhan-Hui
experimental part, p. 2576 - 2584 (2011/10/18)
A novel, environmentally friendly procedure has been developed for the preparation of secondary or tertiary amines by one-pot reductive amination of carbonyl compounds using sodium borohydride in the presence of a magnetically recoverable sulfonic acid supported on hydroxyapatite-encapsulated-γ- Fe2O3 [γ-Fe2O3@HAP-SO 3H] at room temperature. The catalyst was easily separated from the reaction mixture by applying an external magnet and reused for six cycles without significant loss of catalytic activity.
Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines
Bennett, Jacqueline S.,Charles, Kaitlyn L.,Miner, Matthew R.,Heuberger, Caitlin F.,Spina, Elijah J.,Bartels, Michael F.,Foreman, Taylor
body text, p. 166 - 168 (2010/04/22)
Ethyl L-lactate can be tuned with a cosolvent to create polarity conditions ideal for synthesizing aryl aldimines that crystallize directly out of solution within minutes under ambient conditions in excellent yields and requiring no further purification.
