2568-65-2Relevant articles and documents
N,N,N′,N′-tetramethylmethanediamine - A new reagent for aminomethylation of acetylenes
Shaibakova,Titova,Ibragimov,Dzhemilev
, p. 1126 - 1129 (2008)
A new procedure has been developed for aminomethylation of terminal acetylenes with N,N,N′,N′-tetramethylmethanediamine in the presence of transition metals and lanthanide complexes and salts. The procedure ensures formation of the corresponding N,N-dimethylprop-2-yn-1-amines with high yield and selectivity.
Molecular library obtained by allene insertion into the Pd-C bond of cyclopalladated complexes: Biological and pharmacological evaluation
Sirlin, Claude,Chengebroyen, Jaganaiden,Konrath, Renato,Ebeling, Guenther,Raad, Imad,Dupont, Jairton,Paschaki, Marie,Kotzyba-Hibert, Florence,Harf-Monteil, Colette,Pfeffer, Michel
, p. 1724 - 1731 (2004)
A minilibrary of cationic N-heterocycles has been prepared and evaluated. The potential for the preparation was a result of the high versatility of palladium-mediated chemistry. The synthesis of the novel molecules was based on intramolecular quaternization of tertiary amine attached allylpalladium complexes. The steric and electronic factors of the reaction are discussed. The structures of the synthesized molecules made them candidates for precise biological and pharmacological evaluations. Of the various N-heterocyclic compounds, 2,2-dimethyl-3-methylenenaphtho[de/]quinolizinium showed antibacterial activity at micromolar concentrations. This compound also proved to be a nanomolar competitive antagonist for the channel site of the nicotinic acetylcholine receptor. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Synthesis and Application of Silylene-Stabilized Low-Coordinate Ag(I)-Arene Cationic Complexes
Khan, Shabana,Muhammed, Shahila,Parameswaran, Pattiyil,Parvin, Nasrina,Sen, Nilanjana,Tothadi, Srinu
supporting information, p. 1626 - 1632 (2021/06/28)
We report the first examples of N-heterocyclic silylene-stabilized monocoordinate Ag(I) cationic complexes weakly bound to the free arene rings (C6H6, C6Me6, and C7H8). Further, the application of these electrophilic Ag(I) complexes as catalysts has been investigated toward A3-coupling reactions, which afforded a series of propargylamines in good to excellent yields with low catalyst loading under a solvent-free condition (19 examples).
Aromatic Aza-Claisen Rearrangement of Arylpropargylammonium Salts Generated in situ from Arynes and Tertiary Propargylamines
Han, Lu,Li, Sheng-Jun,Zhang, Xue-Ting,Tian, Shi-Kai
supporting information, p. 3091 - 3097 (2021/01/21)
The charge-accelerated aza-Claisen rearrangement of ammonium salts serves as a key step in the construction of complex nitrogen-containing molecules. However, much less attention has been paid to the aromatic aza-Claisen rearrangement than to the aliphatic one. Herein, we report an unprecedented aromatic aza-Claisen rearrangement of arylpropargylammonium salts, generated in situ from arynes and tertiary propargylamines, delivering structurally diverse 2-propargylanilines in moderate to good yields with high regioselectivity. This rearrangement proceeds in the absence of strong bases or transition metals, is compatible with moisture and air, tolerates a wide variety of functional groups, and is amenable to forming 11- to 13-membered heterocycles with a triple bond. The 2-propargylaniline products were treated with aluminum chloride in ethanol to afford multisubstituted indoles in moderate to excellent yields. Finally, a series of deuterium-labeling experiments was performed to elucidate the reaction mechanism.
Fast heck-cassar-sonogashira (hcs) reactions in green solvents
Cabri, W.,Corbisiero, D.,Daka, A.,Fantoni, T.,Ferrazzano, L.,Martelli, G.,Ricci, A.,Tolomelli, A.,Viola, A.
supporting information, p. 3969 - 3973 (2020/06/08)
The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.
An insight into the novel covalent functionalization of multi-wall carbon nanotubes with pseudopeptide backbones for palladium nanoparticles immobilization: A versatile catalyst towards diverse cross-coupling reactions in bio-based solvents
Afshari, Ronak,Emad Hooshmand, Seyyed,Atharnezhad, Mojtaba,Shaabani, Ahmad
, (2019/11/26)
Materials functionalization with multicomponent reactions (MCRs) has grabbed a lot of attention nowadays due to the integration of outstanding features of MCRs with materials domains. Herein, we put the spotlight on the isocyanides and Meldrum's acid-based MCRs route for the one-pot covalent functionalization of multi-wall carbon nanotubes (MWCNTs) which led to pseudopeptide-decorated MWCNTs with the ability to immobilized palladium nanoparticles and serve as a neoteric catalytic system. Characterization of the synthesized nanocatalyst was carried out by FT-IR, 1H NMR, XRD, SEM, TEM, EDX and TGA. The catalytic activities of the nanocatalyst for diverse carbon-carbon cross-coupling reactions were examined in bio-based solvents. The results showed the catalytic performance of the nanocatalyst for the formation of Csp2-Csp2, Csp-Csp2 and Csp-Csp bonds through homocoupling and intermolecular Ullmann, C[sbnd]H arylation, Mizoroki-Heck, Sonogashira and Glaser coupling reactions with considerable improvements in the yield, reaction times, bio-based media and chemoselectivity of the procedures. Additionally, this method demonstrated a high potential for recycling of heterogeneous catalysts by maintaining their initial performances without any evidence of the Pd leaching.
Practical synthesis of silyl-protected and functionalized propargylamines using nanostructured Ag/TiO2 and Pt/TiO2 as active recyclable catalysts
Mohamed, Yasser M. A.,El Nazer, Hossam A.,Solum, Eirik Johansson
, p. 435 - 445 (2019/02/12)
Abstract: Herein we report the use of Ag/TiO2 and Pt/TiO2 nanocatalysts to promote the synthesis of a series of silyl-protected and functionalized propargylamine derivatives through alkyne–amine–aldehyde (A3) coupling unde
Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides
Erkman, Kristin,J?rving, Ivar,Kaabel, Sandra,Kanger, T?nis,Murre, Aleksandra
, p. 4183 - 4197 (2019/11/14)
A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95percent isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For
Copper-Catalyzed Tandem Sulfuration/Annulation of Propargylamines with Sulfur via C-N Bond Cleavage
Xu, Hong-Hui,Zhang, Xiao-Hong,Zhang, Xing-Guo
, p. 7894 - 7900 (2019/06/27)
Copper-catalyzed aerobic oxidative sulfuration and annulation of propargylamines with elemental sulfur is described. The tandem reaction involves C-N bond cleavage and the formation of multiple C-S bonds, affording 1,2-dithiole-3-thiones in good to excellent yields with good functional group tolerance.
S,S-Complexes of Copper(I) Halides with 1,2-Bis(3,5-dimethyloxazol-4-ylmethylsulfanyl)ethane as New Catalysts for Phenylacetylene Aminomethylation
Akhmetova,Akhmadiev,Nurtdinova,Yanybin,Glazyrin,Ibragimov
, p. 1418 - 1424 (2018/09/11)
New metal–heterocycle S,S-complexes based on Cu(I) binary halides and a polydentate ligand, 1,2- bis(3,5-dimethyloxazol-4-ylmethylsulfanyl)ethane have been prepared. The obtained complexes have demonstrated high catalytic activity in aminomethylation of p
