52884-48-7Relevant academic research and scientific papers
Regioselective Synthesis of N2-Aryl 1,2,3-Triazoles via Electro-oxidative Coupling of Enamines and Aryldiazonium Salts
Baidya, Mrinmay,De Sarkar, Suman,Mallick, Samrat
supporting information, (2022/02/14)
An efficient synthetic route for the construction of N2-aryl 1,2,3-triazoles is reported via sequential C-N bond formation and electro-oxidative N-N coupling under metal-free conditions. Readily accessible 2-aminoacrylates and aryldiazonium salts were used as starting materials, and the developed protocol displays excellent functional group tolerance, allowing an extensive range of substrate scope up to 91% isolated yield. Various mechanistic studies, along with the isolation of an intermediate adduct, refer to successive ionic and radical reaction sequences.
Oxidative umpolung ?±-alkylation of ketones
Shneider, O. Svetlana,Pisarevsky, Evgeni,Fristrup, Peter,Szpilman, Alex M.
supporting information, p. 282 - 285 (2015/03/05)
We disclose a hypervalent iodine mediated ?±-alkylative umpolung reaction of carbonyl compounds with dialkylzinc as the alkyl source. The reaction is applicable to all common classes of ketones including 1,3-dicarbonyl compounds and regular ketones via their lithium enolates. The ?±-alkylated carbonyl products are formed in up to 93% yield. An ionic mechanism is inferred based on meticulous analysis, NMR studies, trapping and crossover experiments, and computational studies.
A copper-mediated oxidative coupling route to 3H- and 1H-indoles from N-aryl-enamines
Drouhin, Pauline,Taylor, Richard J. K.
supporting information, p. 2333 - 2336 (2015/04/22)
A facile copper(II)-mediated C-H bond oxidation and C-C bond formation procedure has been applied to the synthesis of indole derivatives. Intramolecular oxidative coupling of 3,3-disubstituted enamines proceeded using a non-expensive and air-stable copper
Catalytic enantioselective nazarov cyclization: Construction of vicinal all-carbon-atom quaternary stereocenters
Jolit, Anais,Walleser, Patrick M.,Yap, Glenn P. A.,Tius, Marcus A.
supporting information, p. 6180 - 6183 (2014/06/23)
The diastereoselective asymmetric synthesis of vicinal all-carbon-atom quaternary stereocenters is a challenging problem in organic synthesis for which only few solutions have been described. A catalytic asymmetric Nazarov cyclization of fully substituted dienones that provides cyclopentenone derivatives with vicinal quaternary stereocenters in high optical purity and as single diastereoisomers is now reported.
Copper(II) triflate catalyzed amination and aziridination of 2-Alkyl substituted 1,3-dicarbonyl compounds
Ton, Thi My Uyen,Tejo, Ciputra,Tiong, Diane Ling Ying,Chan, Philip Wai Hong
experimental part, p. 7344 - 7350 (2012/06/16)
A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI=NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C-H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2-3 equiv was discovered to result in preferential formal aziridination of the C-C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.
Selective synthesis of α-substituted β-keto esters from aldehydes and diazoesters on mesoporous silica catalysts
Murata, Hiroaki,Ishitani, Haruro,Iwamoto, Masakazu
, p. 4788 - 4791 (2008/12/22)
The titled reactions are effectively catalyzed on mesoporous silica MCM-41 but not on amorphous silica prepared from the same starting materials as those of MCM-41. The ordered porous structure was essential to generate the acid catalysis. Planting of Al or Ti ion improved not only the catalytic activity but also the tolerance to basic functional groups of substrates. The catalytic activity of Al- or Ti-MCM-41 was better than that of SnCl2 and NbCl5 in the homogeneous phase. In particular, Al (or Ti)-MCM-41 was characteristically active for the reaction of aldehydes with α-substituted diazoesters to give 2-substituted-3-oxo propionic acid esters.
Preparation of β-keto esters and β-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles
Katritzky, Alan R.,Wang, Zuoquan,Wang, Mingyi,Wilkerson, Chavon R.,Hall, C. Dennis,Akhmedov, Novruz G.
, p. 6617 - 6622 (2007/10/03)
Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-1 are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylati
MESOMERIC ANIONS. X. METHYLATION OF ALKALI-METAL DERIVATIVES OF SOME 1,3-KETONITRILES
Emelina, E. E.,Ershov, B. A.
, p. 692 - 696 (2007/10/02)
The effect of polar factors on the relative nucleophilicity of the oxygen and carbon reaction centers in the alkali-metal derivatives of 2-(X-benzoyl)acetonitriles, 2-(X-benzoyl)propionitriles, and 2-(X-phenyl)acetylacetonitriles was investigated.During methylation with methyl iodide and methyl p-toluenesulfonate in DMFA the ratio of the C- and O-methylation products for all the investigated compounds decreases with increase in the accepting power of the substituent X.It was shown that the sensitivity of the C-reaction center to the effect of the substituent X is greater than that of the O-center.
