33454-16-9Relevant articles and documents
Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation
Armstrong, David R.,Balloch, Liam,Hevia, Eva,Kennedy, Alan R.,Mulvey, Robert E.,O'Hara, Charles T.,Robertson, Stuart D.
, p. 1234 - 1248 (2011)
Previously we reported that direct zincation of N,N-dimethylaniline by the mixed-metal zincate reagent 1 ((TMEDA)Na(TMP)(t-Bu)Zn(t-Bu)) surprisingly led to meta-metallation (zincation) of the aniline, as manifested in the crystalline complex 2 ((TMEDA)Na(
NEAR-INFRARED NERVE-SPARING BENZO[C]PHENOXAZINE FLUOROPHORES
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Page/Page column 46, (2020/05/07)
Provided are near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.
Scalable Synthesis of Acridinium Catalysts for Photoredox Deuterations
Fischer, Christian,Schneider, Lukas,Sparr, Christof,Zilate, Bouthayna
, p. 4359 - 4365 (2019/11/21)
The continuous development of photocatalytic methods incentivizes the design of organic catalysts to complement the frequently used and precious polypyridyl transition metal systems. Herein, a scalable synthesis of suitable acridinium dyes and their appli
Direct Transformation of Esters into Heterocyclic Fluorophores
Fischer, Christian,Sparr, Christof
supporting information, p. 2436 - 2440 (2018/02/06)
Despite the manifold use of heterocyclic fluorophores, only a fraction of the desired dye diversity can be accessed by contemporary synthetic approaches. Herein, we describe a modular method that converts various carboxylic acid esters directly into a bro
Efficient and Selective N-Methylation of Nitroarenes under Mild Reaction Conditions
Pedrajas, Elena,Sorribes, Iván,Guillamón, Eva,Junge, Kathrin,Beller, Matthias,Llusar, Rosa
, p. 13205 - 13212 (2017/09/12)
Herein, we report a straightforward protocol for the preparation of N,N-dimethylated amines from readily available nitro starting materials using formic acid as a renewable C1 source and silanes as reducing agents. This tandem process is efficiently accomplished in the presence of a cubane-type Mo3PtS4 catalyst. For the preparation of the novel [Mo3Pt(PPh3)S4Cl3(dmen)3]+ (3+) (dmen: N,N′-dimethylethylenediamine) compound we have followed a [3+1] building block strategy starting from the trinuclear [Mo3S4Cl3(dmen)3]+ (1+) and Pt(PPh3)4 (2) complexes. The heterobimetallic 3+ cation preserves the main structural features of its 1+ cluster precursor. Interestingly, this catalytic protocol operates at room temperature with high chemoselectivity when the 3+ catalyst co-exists with its trinuclear 1+ precursor. N-heterocyclic arenes, double bonds, ketones, cyanides and ester functional groups are well retained after N-methylation of the corresponding functionalized nitroarenes. In addition, benzylic-type as well as aliphatic nitro compounds can also be methylated following this protocol.
A general method for N-methylation of amines and nitro compounds with dimethylsulfoxide
Jiang, Xue,Wang, Chao,Wei, Yawen,Xue, Dong,Liu, Zhaotie,Xiao, Jianliang
supporting information, p. 58 - 63 (2014/01/17)
DMSO methylates a broad range of amines in the presence of formic acid, providing a novel, green and practical method for amine methylation. The protocol also allows the one-pot transformation of aromatic nitro compounds into dimethylated amines in the presence of a simple iron catalyst. Not just a solvent: DMSO methylates a broad range of amines in the presence of formic acid, providing a novel, green and practical method for amine methylation. The protocol also allows the one-pot transformation of aromatic nitro compounds into dimethylated amines in the presence of a simple iron catalyst. Copyright
Ruthenium-catalyzed C-H functionalization of arylpyrazoles: Regioselective acylation with acid chlorides
Liu, Po Man,Frost, Christopher G.
supporting information, p. 5862 - 5865 (2013/12/04)
A ruthenium-catalyzed C-H acylation of arylpyrazoles with a variety of acyl chlorides is described. The acylation reaction exhibits good regioselectivity and both aromatic and aliphatic acyl chlorides can be effectively coupled to the arylpyrazoles at the
Directed meta-metalation using alkali-metal-mediated zincation
Armstrong, David R.,Clegg, William,Dale, Sophie H.,Hevia, Eva,Hogg, Lorna M.,Honeyman, Gordon W.,Mulvey, Robert E.
, p. 3775 - 3778 (2007/10/03)
(Figure Presented) Move over directed ortho-metalation, here comes directed meto-metalation. The unprecedented meto-zincation of two anilides by a synergic mixed sodium/zinc dialkyl-amide base is presented. The orientation of the deprotonation of the anil
Towards a new type of aromatic diynes activation : Synthesis of a novel bicyclic enediyne
Raeppel, Stéphane,Toussaint, Dominique,Suffert, Jean
, p. 537 - 539 (2007/10/03)
The aromatic acyclic diynes 2 and 3 have been synthesised in order to test the feasibility of a new activation towards their cyclisation. In addition, a difference of stability between 13 and 20 during the Nozaki-Kishi cyclisation reaction occurs when the aromatic ring possesses or not an intramolecular trigger device. Thus, the aromatic bicyclic enediyne 14 is stable while 21 has not been isolated.
A convenient one pot procedure for N-methylation of aromatic amines using trimethyl orthoformate
Padmanabhan, Seetharamaiyer,Reddy, N. Laxma,Durant, Graham J.
, p. 691 - 699 (2007/10/03)
Aromatic amines react with trimethyl orthoformate in the presence of concentrated sulfuric acid followed by acid hydrolysis to afford mono methylated amines in moderate to good yields.
