75066-70-5

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 62-53-3 aniline 
• 553-54-8 lithium benzoate 
• 124-38-9 carbon dioxide 
• 36122-35-7 2-phenylmaleic anhydride 
• 103-71-9 phenyl isocyanate 
• 611-73-4 Benzoylformic acid 
• 64448-06-2 (N-phenyliminovinylidene)triphenylphosphorane 

Downstream Products

• 6017-78-3 (+/-)-1-phenyl-3-phenylpyrrolidine-2,5-dione 
• 6017-78-3 (S)-1,3-diphenylpyrrolidine-2,5-dione 

Relevant academic research and scientific papers

Application of maleimide compound as chitin synthase inhibitor

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.

Weak Coordinating Carboxylate Directed Rhodium(III)-Catalyzed C-H Activation: Switchable Decarboxylative Heck-Type and [4 + 1] Annulation Reactions with Maleimides

A weakly coordinating carboxylate directing group assisted C-H activation with maleimides leading to novel and switchable decarboxylative Heck-type and [4 + 1] annulation products catalyzed by Rh(III) has been reported. In these reactions, solvents play a

Palladium-catalyzed aerobic oxidative carbonylation of alkynes with amines: a general access to substituted maleimides

A catalytic oxidative carbonylation reaction was developed for the synthesis of polysubstituted maleimides from alkynes and amines with air as a green oxidant. This novel transformation proceeds in the presence of palladium chloride without the need for expensive ligands or additives and has a broad substrate scope affording a variety of maleimides in good to high yields.

Palladium-Catalyzed Carbonylative Cyclization of Terminal Alkynes and Anilines to 3-Substituted Maleimides

Herein, we describe an interesting palladium-catalyzed protocol for the carbonylative synthesis of 3-substituted maleimides. By annulation of simple anilines with terminal alkynes under carbon monoxide pressure, the desired 3-substituted maleimides can be

Hydrogenations without hydrogen: Titania photocatalyzed reductions of maleimides and aldehydes

A mild procedure for the reduction of electron-deficient alkenes and carbonyl compounds is described. UVA irradiations of substituted maleimides with dispersions of titania (Aeroxide P25) in methanol/acetonitrile (1:9) solvent under dry anoxic conditions led to hydrogenation and production of the corresponding succinimides. Aromatic and heteroaromatic aldehydes were reduced to primary alcohols in similar titania photocatalyzed reactions. A mechanism is proposed which involves two proton-coupled electron transfers to the substrates at the titania surface.

One pot synthesis of maleimide and hydantoin by Fe(CO)5 catalyzed [2 + 2 + 1] co-cyclization of acetylene, isocyanate and CO

In the presence of a catalytic amount of Fe(CO)5, terminal acetylenes, isocyanates and CO undergo [2 + 2 + 1] cyclization to form substituted maleimides and hydantoins; when internal alkynes are used, exclusive maleimide formation is observed. While the maleimides can be obtained as the major products, in up to 90% yield, when the reaction is carried out in CO atmosphere, in absence of CO, the hydantoins are formed in up to 87% yield. Formation of maleimides has been shown to occur via the formation of a ferrole intermediate, whereas the hydantoins are proposed to form through successive insertion of isocyanate into the iron-acetylide bond. All compounds were characterized by spectroscopic methods and molecular structures of some compounds were established by single crystal X-ray diffraction method. The Royal Society of Chemistry 2012.

Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors

The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have been described so far. Here, we describe the synthesis of N-substituted maleimides and their pharmacological evaluation on the recombinant human fatty acid amide hydrolase (FAAH) and on the purified human MGL. A few N-arylmaleimides were previously described (Saario, S. M.; Salo, O. M.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Jarvinen, T.; Niemi, R. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-Arachidonoylglycerol in Rat Cerebellar Membranes. Chem. Biol. 2005, 12, 649-656) as MGL inhibitors, and along these lines, we present a new set of maleimide derivatives that showed low micromolar IC50 and high selectivity toward MGL vs FAAH. Then, structure-activity relationships have been investigated and, for instance, 1-biphenyl-4-ylmethylmaleimide inhibits MGL with an IC50 value of 790 nM. Furthermore, rapid dilution experiments reveal that these compounds act as irreversible inhibitors. In conclusion, N-substituted maleimides constitute a promising class of potent and selective MGL inhibitors.

Mesoionic carbenes: Reactions of 1, 3-diphenyltetrazol-5-ylidene with electron-deficient alkenes, and synthesis and catalytic activities of the (tetrazol-5-ylidene)rhodium(I) complexes

The reactions of 1, 3-diphenyltetrazol-5-ylidene, a rare example of mesoionic carbenes, with electron- deficient unsaturated compounds were studied. The carbene reacted with dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylate to give a 5-tetrazoliomethylide, together with hydrazine derivatives. The reaction with tetracyanoethylene gave another methylide in low yield. On the contrary, the reactions with weaker electrophiles, such as 3, 6-diphenyl-1, 2, 4, 5-tetrazine, fumalonitrile, N-phenylmaleimide, and dimethyl acetylenedicarboxylate, did not give any coupling products, but gave phenylated products and/or Michael addition products via the degradation of the 1, 3-diphenyltetrazole ring. Novel mesoionic mono- and bis(carbene)-rhodium(I) complexes were synthesized and the structures were characterized by X-ray crystallography. Their catalytic activities for the decarbonylative addition reaction of benzoyl chloride to ethynylbenzene were investigated.

Cumulated Ylides, XVII. Synthesis of Cyclic Compounds from Triphenylphosphorane and Oxocarboxylic Acids - A Novel Method for Anellation

By entropically supported intramolecular Wittig reaction from α-keto carboxylic acids 23 with triphenylphosphorane (1) N-phenylmaleinisoimides 26 and -imides 29 are formed.The compounds 26 can be rearranged into 29 with a catalytic amount of sodium azide. - From γ-keto carboxylic acids 30 3-substituted 2-cyclopenten-1-ones 37 can be derived via the 3,6-dioxo-2-(triphenylphosphoranylidene)alkananilides 33.Analogously, 3-substituted 2-cyclohexen-1-ones 49 are formed from δ-keto carboxylic acids 46. o-Acylbenzoic acids 38, in the case R = H, are converted with 1 into the benzazepinedione derivative 44, and in the case R unlike H into 3-substituted 1-oxo-1H-indene-2-carboxanilides 45. - Starting from oxo carboxylic acids, possessing the carbonyl function in a ring, five- and six-membered rings can be anellated in a simple way.

Process for preparation of substituted olefins

The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.