3152-16-7Relevant academic research and scientific papers
Approach to the Synthesis of Unsymmetrical/Symmetrical Maleimides via Desulfitative Arylation at Different Temperatures
Abbasnia, Masoumeh,Sheykhan, Mehdi,Ghaffari, Tahereh,Safari, Elham
, p. 11688 - 11698 (2020/10/23)
New routes toward selective synthesis of both mono-and diaryl maleimides have been innovated. The mere requirement to this end is through the increase of temperature. The method works effectively for maleic anhydride and maleic acid as well. Also, the fir
Synthesis of anti-tubercular marine alkaloids denigrins A and B
Karak, Milandip,Oishi, Tohru,Torikai, Kohei
, p. 2800 - 2803 (2018/06/15)
The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.
Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides
Han, Zhengyu,Wang, Rui,Gu, Guoxian,Dong, Xiu-Qin,Zhang, Xumu
, p. 4226 - 4229 (2017/04/21)
Asymmetric hydrogenation of various 3-substituted maleic anhydrides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) under mild conditions was successfully developed. A wide range of 3-alkyl and 3-aryl maleic anhydrides were hydrogenated well to provide the desired products 3-substituted succinic anhydrides in one hour with excellent results (full conversions, up to 99% yield, 99% ee, 3000 TON). Importantly, we developed a creative and efficient synthetic route to construct the key intermediate of the hypoglycemic drug mitiglinide through our catalytic system.
Efficient electrochemical dicarboxylations of arylacetylenes with carbon dioxide using nickel as the cathode
Yuan, Gao-Qing,Jiang, Huan-Feng,Lin, Chang
, p. 5866 - 5872 (2008/09/21)
The electrochemical dicarboxylation of arylacetylenes with carbon dioxide could be smoothly achieved in an undivided cell using Ni as the cathode and Al as the anode with n-Bu4NBr-DMF as the supporting electrolyte, at a constant current under CO2 pressure of 3 MPa and room temperature in the absence of additional catalysts. The corresponding aryl-maleic anhydrides and 2-arylsuccinic acids were afforded in excellent total yields (82-94%). Under anhydrous conditions, an unsaturated aryl-maleic anhydride as the main product was obtained, while the presence of H2O would lead to the formation of saturated 2-arylsuccinic acids. The results of cyclic voltammetric experiments show that a nickel cathode itself plays the catalytic role in the reduction reaction of arylacetylenes with CO2.
Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: Synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and Polycitrin A
Burtoloso, Antonio Carlos B.,Garcia, Ariel L. L.,Miranda, Karen C.,Correia, Carlos Roque D.
, p. 3145 - 3149 (2008/02/13)
The Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates was investigated. Symmetrical and unsymmetrical 3,4-diarylmaleic anhydrides, some of them showing interesting fluorescent properties, were prepared in one or two steps from ch
A simple, convenient method for the synthesis of maleic anhydrides from α-keto esters and alkanoic acid anhydrides using the TiCl 4/n-Bu3N reagent system
Kishorebabu, Neela,Periasamy, Mariappan
, p. 2107 - 2109 (2007/10/03)
Reaction of α-keto esters with alkanoic acid anhydrides using the TiCl4/n-Bu3N reagent system gives the corresponding maleic anhydrides in 62-95% yields.
1-(2-Iodophenyl)-1H-tetrazole as a ligand for Pd(II) catalyzed Heck reaction
Gupta, Arun Kumar,Song, Chung Hyun,Oh, Chang Ho
, p. 4113 - 4116 (2007/10/03)
1-(2-Iodophenyl)-1H-tetrazole 2 was synthesized by the reaction of 2-iodoaniline, sodium azide and triethyl orthoformate in acetic acid. The newly synthesized ligand 2 was successfully used in Heck reaction to give the cross-coupled products in excellent yields.
Synthesis of maleic anhydrides and maleic acids by Pd-catalyzed oxidative dicarbonylation of alk-1-ynes
Gabriele, Bartolo,Veltri, Lucia,Salerno, Giuseppe,Costa, Mirco,Chiusoli, Gian Paolo
, p. 1722 - 1728 (2007/10/03)
We have found that carbon dioxide effectively promotes the Pd-catalyzed oxidative carbonylation of terminal alkynes to give maleic anhydrides in fair yields. Reactions were carried out in aqueous dioxane at 60-80 °C in the presence of catalytic amounts of PdI2 in conjunction with KI and under a 4:1:10 mixture of CO/air/CO2 (60 atm total pressure at 25 °C). By working in the presence of a large excess of water, maleic acids were formed selectively with unprecedented catalytic efficiencies for this kind of reaction. In the latter case, the use of an excess of carbon dioxide tended to inhibit, rather than promote, the reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Carbonylation of terminal alkynes using a multicatalytic system, Pd(II)/chlorohydroquinone/NPMoV, under carbon monoxide and dioxygen
Sakurai, Yasunori,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 1701 - 1704 (2007/10/03)
Carbonylation of terminal alkynes was performed using a new triple catalytic system, Pd(II)/chlorohydroquinone/NPMoV, under carbon monoxide and oxygen. For instance, phenylacetylene was converted into methyl phenylpropiolate (85%) in methanol and phenylmaleic anhydride (62%) in dioxane. The reaction did not take place in the absence of oxygen.
