15286-48-3Relevant academic research and scientific papers
Simple and High Yield Synthesis of Aldimines via Palladium Complex-Catalyzed Reduction of Imidoyl Chlorides
Tanaka, Masato,Kobayashi, Toshi-aki
, p. 967 - 969 (1985)
Imidoyl chlorides 1 were efficiently reduced to aldimines 2 by molecular hydrogen in the presence of triethylamine and a catalytic amount of bispalladium dichloride
Development of a straightforward and efficient protocol for the one-pot multicomponent synthesis of substituted alpha-aminoallylphosphonates under catalyst-free condition
Brahmachari, Goutam,Begam, Sanchari,Karmakar, Indrajit,Gupta, Vivek K
supporting information, p. 769 - 779 (2021/05/12)
A catalyst-free practical version of Kabachnik-Fields strategy has been developed for the efficient and straightforward one-pot synthesis of diversely substituted α-aminoallylphosphonates, a limitedly reported class of biologically important α-aminophosph
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.
Stereoselective Construction of γ-Lactams via Copper-Catalyzed Borylacylation
Bajohr, Jonathan,Lautens, Mark,Polishchuk, Iuliia,Torelli, Alexa,Whyte, Andrew
supporting information, p. 7915 - 7919 (2020/11/02)
A versatile and highly stereoselective borylative cyclization to generate polyfunctionalized γ-lactams has been developed. The stereoselective synthesis of these key ring systems is crucial due to their ubiquity in natural products. We report the diastero- and enantioselective construction of di- and trisubstituted γ-lactam cores, with examples containing an enantioenriched quaternary carbon.
Stereoselective synthesis, spectroscopic and X-ray crystallographic characterization of novel trans- and cis-3-methylseleno substituted monocyclic β-lactams: Potential synthons for C-3 functionalized/bicyclic/halospiroseleno-β-lactams of medicinal interes
Bhalla, Aman,Nagpal, Yogesh,Berry, Shiwani,Narula, Dipika,Bari,Bhasin,Kumar, Rajeev
, p. 172 - 182 (2018/03/24)
New series of trans- and cis-3-methylseleno substituted β-lactams (4, 5) have been prepared from 2-methylselenoethanoic acid (2). The four-membered β-lactam ring was introduced by the condensation reaction between ketene retrieved from 2-methylselenoethan
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).
Reactions of Secondary Allylamines with Bis(n5:n1-pentafulvene)titanium Complexes: Selective Formation of Monoazabutadiene Titanium Complexes by N-H and C-H Bond Activation
Man?en, Manfred,T?ben, Iris,Kahrs, Christoph,B?lte, Jens-Henning,Schmidtmann, Marc,Beckhaus, Rüdiger
supporting information, p. 2973 - 2981 (2017/08/21)
The N-H and C-H bond activation reactions at ambient conditions of seven different secondary allyl amines (Aa-g) with bis(n5:n1-pentafulvene)titanium complexes (1) have been investigated. Bis(n5:n1-adamantyliden
Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides
Braunstein, Hannah,Langevin, Spencer,Khim, Monique,Adamson, Jonathan,Hovenkotter, Katie,Kotlarz, Lindsey,Mansker, Brandon,Beng, Timothy K.
supporting information, p. 8864 - 8872 (2016/10/03)
A modular substrate-controlled hexannulation of inherently promiscuous 1,3-azadienes with hexacyclic anhydrides, which affords versatile vicinally functionalized allylic lactams, in high yields, regio- and stereoselectivities is described.
