3152-15-6Relevant articles and documents
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 (1999)
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.
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.
Expeditious synthesis of the marine natural products prepolycitrin a and polycitrins a and b through heck arylations
Canto, Karen,Da Silva Ribeiro, Rodrigo,Biajoli, Andre F. P.,Correia, Carlos Roque D.
, p. 8004 - 8013 (2014/01/06)
New, efficient protocols for the syntheses of the marine natural products prepolycitrin A as well as polycitrins A and B were developed by employing the Heck-Matsuda arylation of maleic anhydride or dimethyl fumarate with aryldiazonium tetrafluoroborates. Both symmetrical and unsymmetrical 3,4-diarylmaleic anhydrides were easily and effectively prepared. Efficient bromination reactions that employed tribromoisocyanuric acid provided access to the polycitrin family of compounds. Under microwave irradiation in the presence of tyramine, the corresponding maleimides were obtained in high yields from the brominated 3,4-diarylmaleic anhydrides. This methodology provided for the concise synthesis of prepolycitrin A and the total syntheses of the marine alkaloids polycitrins A and B in overall yields of 37 and 47 % from maleic anhydride and dimethyl fumarate, respectively. The efficient and concise syntheses of the marine natural products prepolycitrin A as well as polycitrins A and B were accomplished by using a Heck-Matsuda arylation of maleic anhydride with aryldiazonium tetrafluoroborates. Polycitrins A and B were synthesized in overall yields of 37 and 47 %, respectively. Copyright
Arylmaleic anhydrides via Heck arylation of fumaric acid
Roshchin, Alexander I.
experimental part, p. 3633 - 3635 (2010/08/13)
Palladium-catalyzed arylation of fumaric acid with aryl iodides is found to be a very simple, economic and scalable approach to arylmaleic anhydrides. The reaction is facilitated by the presence of donor moieties on the aryl fragment and does not occur wi
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.
Fungicidal agents containing pyrrolidones as their active agents and use thereof for treating plants
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, (2008/06/13)
Agrochemical compositions having fungicidal action and comprising as active compounds compounds of the formula I where R1is hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, formyl or C1-C6
Facile synthesis of arylmaleic acids and anhydrides
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, (2008/06/13)
A process for making acrylmaleic acid and arylmaleic anhydride derivative useful as intermediates for the preparation of arylmaleimides in the synthesis of compounds having activity in the central nervous system. The process involves reacting arylacetonitriles with glyoxylic acid to provide novel intermediate 3-aryl-3-cyanopropeneoates which may be converted to the arylmaleic acid and arylmaleic anhydride derivatives.
