105-53-3Relevant articles and documents
Octacarbonyl dicobalt-catalyzed selective transformation of ethyl diazoacetate into organic products containing the ethoxycarbonyl carbene building block
Tuba, Robert,Ungváry, Ferenc
, p. 59 - 67 (2003)
In the presence of 1 mol% octacarbonyl dicobalt ethyl diazoacetate can be transformed at room temperature and carbon monoxide pressure selectively into diethyl 2-diazo-3-oxo-pentanedicarboxylate or in the presence of an alcohol (methanol, ethanol, tert-bu
Indium as a reducing agent. Chemoselective reduction of α-halocarbonyl compounds and benzyl halides by indium metal in water under sonication
Ranu, Brindaban C.,Dutta, Pinak,Sarkar, Arunkanti
, p. 1139 - 1140 (1999)
Indium metal in water reduces a-halocarbonyl compounds and benzyl iodides to the corresponding dehalogenated products in excellent yields under sonication although simple alkyl and aryl iodides remained inert under these conditions.
An unusual synthesis of malonates
Barton, Derek H. R.,Langlois, Pascal,Okano, Takashi,Ozbalik, Nubar
, p. 325 - 326 (1990)
The reaction of palladium diacetate, triethylamine, ethyl chlorocarbonate and carbon monoxide in acetonitrile at room temperature gives a good yield of diethyl malonate. By 13C labelling of each of the reagents in turn it has been proven that the methylene group of the malonate comes from an acetate originally bonded to PdII.
Mechanism of the cobalt-catalyzed carbonylation of ethyl diazoacetate
Ungvári, Neszta,F?rdos, Eszter,Kégl, Tamás,Ungváry, Ferenc
, p. 2016 - 2028 (2010)
Carbonyl cobalt complexes serve as catalysts or catalyst precursors for the facile and selective transformation of primary diazoalkanes into the corresponding ketene. The mechanism of this carbonylation reaction has been elucidated in the case of ethyl diazoacetate as model diazoalkane using octacarbonyl dicobalt as the catalyst precursor. Dinuclear cobalt complexes having ethoxycarbonylcarbene ligand(s) in bridging position(s) have been identified as active intermediary of the catalytic cycles and their relevant chemical properties have been explored. Key step of the carbonylation is the formation of the highly reactive ethoxycarbonylketene by intramolecular coupling of a carbonyl ligand with the ethoxycarbonylcarbene ligand. DFT calculations reveal that the ketene formation takes place via a rapid coupling of the carbene ligand with one terminal CO followed by coordination of an external carbon monoxide and by a facile intramolecular rearrangement and ketene elimination. The ethoxycarbonylketene can be in situ trapped by OH, NH, or CH acid compounds or by N-substituted imines. In the presence of ethanol diethyl malonate is the only product of the catalytic carbonylation of ethyl diazoacetate. On the bases of the kinetics of the composing steps of the catalytic cycles, localization of the rate-determining step(s) under various reaction conditions has been made.
Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: Novel methylenepyrrolidine and methylenetetrahydrofuran syntheses
Morikawa, Satoshi,Yamazaki, Shoko,Furusaki, Yoshiteru,Amano, Naoya,Zenke, Kazumi,Kakiuchi, Kiyomi
, p. 3540 - 3544 (2006)
A new zinc- and indium-promoted conjugate addition-cyclization reaction to afford nitrogen- and oxygen-containing five-membered heterocycles has been developed. Reaction of ethenetricarboxylates with propargylamines (1 equiv) in the presence of ZnBr2 or InBr3 afforded methylenepyrrolidines in high yields. The stoichiometric use of ZnBr2 or InBr3 at room temperature and the catalytic use of InBr 3-Et3N at 80°C were effective. Reaction of ethenetricarboxylates with propargyl alcohol in the presence of ZnBr2 or InBr3 afforded methylenetetrahydrofurans.
Synthesis of monoesters and diesters using eco-friendly solid acid catalysts - Cerium(IV) and thorium(IV) phosphates
Parangi, Tarun,Wani, Bina,Chudasama, Uma
, p. 430 - 438 (2013)
In the present endeavour, amorphous cerium phosphate (CP) and thorium phosphate (TP) have been synthesized by sol-gel method and also under microwave irradiation to yield CPM and TPM. CP, TP, CPM and TPM have been characterized for elemental analysis (ICP-AES), spectral analysis (FTIR), thermal analysis (TGA), X-ray diffraction studies, SEM, EDX, surface area (BET) and surface acidity (NH3-TPD). The potential use of these materials as solid acid catalysts has been explored by studying esterification as a model reaction. Monoesters such as ethyl acetate (EA), propyl acetate (PA), butyl acetate (BA), benzyl acetate (BzAc) and diesters such as diethyl malonate (DEM), diethyl succinate (DES), dibutyl phthalate (DBP), dioctyl phthalate (DOP) have been synthesized. Esterification conditions have been optimized by varying several parameters such as reaction time, catalyst amount and mole ratio of reagents. The catalytic activity has been compared and correlated with reference to surface acidity of the catalysts. It is found that catalytic activity of CPM > CP > TP M > TP. The regenerated catalysts could be reused upto two catalytic runs without significant loss in % yields of esters formed. The highlighting feature of the present work is the catalysts CPM and TPM that are synthesized in a much shorter reaction time with higher surface acidity giving good % yield of esters.
The synthesis of polymeric catalyst using ion exchange resin and its application for esterification
Whang,Lee,Lee
, p. 2341 - 2342 (1984)
The copolymer complexes have been synthesized from cation and/or anion resin with metal catalyst such as aluminum chloride or iron(III) chloride. Electron microprobe X-ray analysis demonstrated that aluminum and iron were distributed uniformly in the copolymer complex. The catalytic activity for esterification of dibasic organic acids was discussed and showed that copolymer complex from porous type cation exchange resin was much better catalyst than that from gel type. Copolymer complexes have been synthesized from cation and/or anion resin with metal catalyst such as aluminum chloride or iron (III) chloride. Electron microprobe X-ray analysis demonstrated that aluminum and iron were distributed uniformly in the copolymer complex. The catalytic activity for esterification of dibasic organic acids was discussed and showed that copolymer complex from the porous type cation exchange resin was a much better catalyst than that from the gel type.
Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents
Jin, Guofan,Li, Zhenwang,Qi, Xueyong,Sun, Xianyu,Xiao, Fuyan,Zhao, Lei
, (2020)
A series of novel quinoline and quinolinium iodide derivatives were designed and synthesized to discover potential anticancer and antibacterial agents. With regard to anticancer properties, in vitro cytotoxicities against three human cancer cell lines (A-549, HeLa and SGC-7901) were evaluated. The antibacterial properties against two strains, Escherichia coli (ATCC 29213) and Staphylococcus aureus (ATCC 8739), along with minimum inhibitory concentration (MIC) values were evaluated. The target alkyliodine substituted compounds exhibited significant antitumor and antibacterial activity, of which compound 8-((4-(benzyloxy)phenyl)amino)-7-(ethoxycarbonyl)-5-propyl-[1,3]dioxolo[4,5-g]quinolin-5-ium (12) was found to be the most potent derivative with IC50 values of 4.45±0.88, 4.74±0.42, 14.54±1.96, and 32.12±3.66 against A-549, HeLa, SGC-7901, and L-02 cells, respectively, stronger than the positive controls 5-FU and MTX. Furthermore, compound 12 had the most potent bacterial inhibitory activity. The MIC of this compound against both E. coli and S. aureus was 3.125 nmol ? mL?1, which was smaller than that against the reference agents amoxicillin and ciprofloxacin.
Co2(CO)8-induced domino reactions of ethyl diazoacetate, carbon monoxide and ferrocenylimines leading to 2-(1-ferrocenyl-methylidene)-malonic acid derivatives
Balogh, János,Kégl, Tamás,Ungváry, Ferenc,Skoda-F?ldes, Rita
, p. 4727 - 4730 (2009)
Novel 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained upon reacting ethyl diazoacetate, carbon monoxide and ferrocenylimines in the presence of Co2(CO)8 as catalyst under mild conditions. Presumably, the reaction involves three steps taking place in a domino fashion, (i) carbonylation of ethyl diazoacetate leading to a ketene derivative, (ii) [2+2] cycloaddition of the ketene with the ferrocenylimine present in the reaction mixture resulting in the formation of a β-lactam and (iii) N(1)-C(4) cleavage of the β-lactam ring. In most cases, 2-(1-ferrocenyl-methylidene)-malonic acid derivatives are obtained as a separable mixture of E- and Z-isomers in ratios depending on the structure of the imine component.
Rhodium-catalyzed double carbonylation of diiodomethane in the presence of triethylorthoformate
Cheong, Minserk,Kim, Mi-Na,Shim, Ji Yeon
, p. 253 - 255 (1996)
Catalytic double carbonylation of diiodomethane in triethylorthoformate in the presence of a homogeneous rhodium complex gives diethylmalonate in a fairly good yield.
