4665-00-3Relevant articles and documents
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.
Fluorescence from bisaryl-substituted maleimide derivatives
Lauer, Milena Helmer,Drekener, Roberta Lopes,Correia, Carlos Roque Duarte,Gehlen, Marcelo Henrique
, p. 859 - 866 (2014/06/09)
A series of bisaryl-substituted fluorescent maleimides was synthesized via the Heck arylation. The compounds showed broad fluorescence emission bands in the visible region, a large Stokes shift in polar solvents and emission quantum yields varying from 0.
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
High-pressure-assisted addition of (methoxyphenyl)maleic anhydrides to dienes. Synthesis of 3a-aryltetrahydroisoindole-1,3-diones
Roshchin,Kuznetsov,Polunin
, p. 509 - 512 (2008/04/05)
A new synthesis of (2-and 4-methoxyphenyl)maleic anhydrides was accomplished, the reactions of which with cyclopentadiene and 3-sulfolene, serving as a 1,3-butadiene equivalent, furnished the [4+2]-cycloadducts. The latter were converted into imides of 2-
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.
A facile synthesis of rubrolide E1
Kar, Anirban,Argade, Narshinha P.
, p. 2284 - 2286 (2007/10/03)
A simple and efficient synthesis of rubrolide E (1e) has been demonstrated via Meerwein coupling reaction of para-anisyldiazonium chloride with N-phenylmaleimide (2), regioselective reduction of para-anisylmaleic anhydride (4), Knoevenagel condensation of butyrolactone 5 with para-anisaldehyde and demethylation pathway. Georg Thieme Verlag Stuttgart.
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.
