153407-55-7

Upstream product

• 95-53-4 o-toluidine 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 10468-64-1 o-tolyl isocyanide 
• 110-82-7 cyclohexane 
• 88-72-2 1-methyl-2-nitrobenzene 
• 3289-28-9 ethyl cyclohexanecarboxylate 
• 615-37-2 ortho-methylphenyl iodide 
• 1122-56-1 cyclohexylcarboxamide 
• 31656-92-5 1-azido-2-methyl-benzene 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 13141-48-5 2-cyclohexyl-1H-indole 
• 1416576-68-5 C₂₄H₂₇NO₄ 
• 1416576-67-4 C₂₃H₂₇NO₃S 

Relevant academic research and scientific papers

Iron-Catalyzed Oxidative Coupling Reaction of Isocyanides and Simple Alkanes towards Amide Synthesis

An iron-catalyzed oxidative coupling reaction of isocyanide and readily available alkane has been disclosed. In the presence of a catalytic amount of FeCp2 (10 mol%), heating a mixture of alkane, isocyanide, and DTBP in DCE allows for the formation of an amide. This reaction tolerates many simple alkanes including cycloalkanes and chain alkanes. Furthermore, a series of aromatic isocyanides having different substituents on the aromatic ring are also proven to be effective reaction components. Unfortunately, the employment of aliphatic isocyanides fails to afford the desired products. The present strategy avoids tedious procedures and the employment of toxic starting materials, thus providing an environmentally benign and efficient protocol towards amide synthesis. (Figure presented.).

Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes

Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes

Aryl amides have been used as important compounds in pharmaceuticals, materials and in molecular catalysis. The methods reported to prepare aryl amides generally require very specific reagents, and the most popular carboxyl-amine coupling reactions demand stoichiometric activators. Herein, we report that aryl azides react with aldehydes under base-catalyzed conditions to yield aryl amides efficiently. Mechanistic investigations support the formation of triazoline intermediates via azide-enolate cycloaddition, which subsequently undergo rearrangement to give amides by either thermal decomposition (20-140 °C) or aqueous acid work-up at room temperature. The strategy does not require nucleophilic anilines and is especially efficient for highly electron-deficient aryl amides, including perfluoroaryl amides, which are otherwise challenging to synthesize.

Mild and efficient palladium-catalyzed direct trifluoroethylation of aromatic systems by C-H activation

The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.

Green alternative solvents for the copper-catalysed arylation of phenols and amides

Investigation of the use of green organic solvents for the Cu-catalysed arylation of phenols and amides is reported. Alkyl acetates proved to be efficient solvents in the catalytic processes, and therefore excellent alternatives to the typical non-green solvents used for Cu-catalysed arylation reactions. Solvents such as isosorbide dimethyl ether (DMI) and diethyl carbonate also appear to be viable possibilities for the arylation of phenols. Finally, a novel copper catalysed acyl transfer process is reported.

Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors

New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized 5. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCI/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.