10354-53-7Relevant articles and documents
Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy
Suveges, Nícolas S.,de Souza, Rodrigo O. M. A.,Gutmann, Bernhard,Kappe, C. Oliver
, p. 6511 - 6517 (2017)
Herein we report a convenient, fast, and high-yielding method for the generation of the racemic amide anaesthetics mepivacaine, ropivacaine, and bupivacaine. Coupling of α-picolinic acid and 2,6-xylidine under sealed-vessel microwave conditions generates the intermediate amide after a reaction time of only 5 min at 150 °C. Subsequent reaction in a continuous-flow high-pressure hydrogenator (H-Cube ProTM) in the presence of the respective aldehyde directly converts the intermediate to the final amide anaesthetics in a continuous, integrated, multi-step ring-hydrogenation/reductive amination protocol. Merits and limitations of the protocol are discussed.
Pyridyl-decorated self-folding heptaamide cavitands as ligands in the rhodium-catalyzed hydrogenation of norbornadiene
Korom, Sasa,Ballester, Pablo
, p. 4276 - 4282 (2014)
The different binding geometries exhibited in solution by the Rh I cationic complexes of three regioisomeric self-folding heptaamide cavitands, each decorated with one pyridyl group at the upper rim, are taken into account to explain the diverse distributions of products obtained when these complexes are employed as catalysts for the hydrogenation of norbornadiene. Copyright
N-picolinamides as ligands for Ullmann-type homocoupling reactions
Damkaci, Fehmi,Altay, Esra,Waldron, Matthew,Knopp, Michael A.,Snow, David,Massaro, Nicholas
, p. 690 - 693 (2014)
The use of N-phenylpicolinamide (NPPA) as a ligand in Ullmann-type homocoupling reactions of aryl iodides and bromides in common solvents, such as DMF and MeCN has been successfully demonstrated at room temperature. In addition, this work provided the first example of the homocoupling of an aryl chloride at 82 °C, which is a relatively low temperature when compared to regular Ullmann reaction temperatures. Also, NPPA was successfully employed in base-and heat free Suzuki reactions, including electron rich and poor aryl halides with heteroarylboronic acids in moderate yields.
Copper-promoted C-N bond cross-coupling with phenylstannane
Lam, Patrick Y.S.,Vincent, Guillaume,Bonne, Damien,Clark, Charles G.
, p. 3091 - 3094 (2002)
Copper-promoted C-N bond cross-coupling of NH-containing substrates with phenylstannane at room temperature was accomplished with the addition of TBAF.
Reaction of N-fluoropyridinium fluoride with isonitriles and diazo compounds: A one-pot synthesis of (pyridin-2-yl)-1H-1,2,3-triazoles
Kiselyov, Alexander S.
, p. 2631 - 2634 (2006)
Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles and diazo compounds led to the formation of the corresponding (pyridine-2-yl)-1H-1,2,3-triazoles in good yields (37-59%). Best outcome was consistently achieved with bo
Copper-Catalyzed C-4 Carboxylation of 1-Naphthylamide Derivatives with CBr4/MeOH
Sahoo, Tapan,Sen, Chiranjit,Singh, Harshvardhan,Suresh,Ghosh, Subhash Chandra
, p. 3950 - 3957 (2019)
A simple and practical copper catalyzed C-4 carboxylation reaction of 1-naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4-H functi
Rh(III)-catalyzed cascade oxidative olefination/cyclization of picolinamides and alkenes via C-H activation
Cai, Shangjun,Chen, Chao,Shao, Peng,Xi, Chanjuan
, p. 3142 - 3145 (2014)
Rh(III)-catalyzed cascade oxidative alkenylation/cyclization of picolinamides and alkenes to furnish pyrido pyrrolone derivatives is described, in which three C-H bonds and one N-H bond broke, while one C-C bond and one C-N bond formed. The reaction proceeded with high yield and high regioselectivity and stereoselectivity. Moreover, copper acetate can also be used in catalytic amounts with O2 serving as the terminal oxidant.
α-nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid
Lam, Patrick Y.S.,Deudon, Sophie,Hauptman, Elisabeth,Clark, Charles G.
, p. 2427 - 2429 (2001)
Heteroarylcarboxamides containing α-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organ
Acetato(N-phenyl-pyridine-2-carbox-amidato-k2 N,N)(N-phenyl-pyridine-2-carboxamide-k2 N 1,O)copper(II)
Gomes, Ligia,Low, John Nicolson,Valente, Mario A.D.C.,Freire, Cristina,Castro, Baltazar
, p. m293-m296 (2007)
The title complex, [Cu(C12H9N2O)(C2H3O2)(C12H10N2O)], is a neutral Cu II complex with a primary N3O2 coordination sphere. The Cu centre coordinates to both a deprotonated and a neutral mol-ecule of N-phenyl-pyridine-2-carboxamide and also to an
Synthesis, characterization and antitumor activity of novel gold (III) compounds with cisplatin-like structure
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Gold(III) centers are isoelectronic to Pt(II) compounds and adopt square-planar configurations similar to that of cisplatin, gold (III) compounds could display strong effects of tumor cell growth inhibition by a non-cisplatin-like mode of action. In our present work, we synthesized and characterized three gold(III) complexes which are coordinated by the N atom of amide group and investigated their in vitro anticancer activity, including their mechanism of action. In screening their in vitro activity, we found three gold complexes to exhibit selectivity of cytotoxicity, and complex 3 display better anticancer activity than another two gold(III) compounds and cisplatin. The three gold (III) complexes show preference to accumulation in mitochondria. The complex 3 could inhibit the growth of tumor cell by inducing the apoptosis mediated by ER-stress through loss of cellular homeostasis disrupts Ca2+ signaling. Based on our results, we believe complex 3 to be a promising anticancer agent or lead compound for further anticancer drug development.
