85829-29-4

Upstream product

• 95-49-8 2-methylchlorobenzene 
• 79-37-8 oxalyl dichloride 
• 22084-89-5 3-(2-methylphenyl)propanoic acid 
• 78606-96-9 <(2-methylphenyl)methyl>propanedioic acid 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 6619-57-4 diethyl 2-(2-methylbenzyl)-malonate 

Downstream Products

• 103857-85-8 3-o-tolyl-propionic acid methylamide 
• 90266-00-5 1-Diazo-4-(2-methylphenyl)butan-2-one 
• 31701-18-5 8-Methyl-2-tetralone 
• 326816-46-0 N-[(3-Chloro-5-trifluoromethyl-2-pyridyl)methyl]-3-(2-tolyl)propionamide 
• 1267874-67-8 1,1,1-trifluoro-4-(o-tolyl)butan-2-one 
• 1400792-53-1 N-methoxy-N-methyl-3-(o-tolyl)propanamide 
• 133131-48-3 4-methyl-indan-1-one-(2,4-dinitro-phenylhydrazone) 

Relevant academic research and scientific papers

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Visible-Light Induced C(sp2)?H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical–Polar Crossover

We report an approach for the intramolecular C(sp2)?H amidation of N-acyloxyamides under photoredox conditions to produce δ-benzolactams with an aryl-alkyl σ-bond relocation. Computational studies on the designed reductive single electron transfer strategy led us to identify N-[3,5-bis(trifluoromethyl)benzoyl] group as the most effective amidyl radical precursor. Upon the formation of an azaspirocyclic radical intermediate by the selective ipso-addition with outcompeting an ortho-attack, radical–polar crossover was then rationalized to lead to the rearomative ring-expansion with preferential C?C bond migration.

Selective Inhibitors of a Human Prolyl Hydroxylase (OGFOD1) Involved in Ribosomal Decoding

Human prolyl hydroxylases are involved in the modification of transcription factors, procollagen, and ribosomal proteins, and are current medicinal chemistry targets. To date, there are few reports on inhibitors selective for the different types of prolyl hydroxylases. We report a structurally informed template-based strategy for the development of inhibitors selective for the human ribosomal prolyl hydroxylase OGFOD1. These inhibitors did not target the other human oxygenases tested, including the structurally similar hypoxia-inducible transcription factor prolyl hydroxylase, PHD2.

Carboxy Group as a Remote and Selective Chelating Group for C?H Activation of Arenes

The first example of carboxy group assisted, remote-selective C(sp2)?H activation with a PdII catalyst has been developed and proceeds through a possible κ2 coordination of the carboxy group, thus suppressing the ortho-C?H activation through κ1 coordination. Besides meta-C?H olefination, direct meta-arylation of hydrocinnamic acid derivatives with low-cost aryl iodides has been achieved for the first time. These findings may motivate the exploration of novel reactivities of the carboxy assisted C?H activation reactions with intriguing selectivities.

Rh(III)-Catalyzed meta-C-H Olefination Directed by a Nitrile Template

A range of Rh(III)-catalyzed ortho-C-H functionalizations have been developed; however, extension of this reactivity to remote C-H functionalizations through large-ring rhodacyclic intermediates has yet to be demonstrated. Herein we report the first examp

Ligand-Assisted Palladium(II)/(IV) Oxidation for sp3C H Fluorination

The direct functionalization of inert sp3C H bonds is limited to a few bond types. Although the activation of sp3C H bonds can be accomplished under mild conditions using palladium catalysts, the subsequent functionalization is not trivial due to the high energy required to convert palladium(II) to palladium(IV). We have systematically studied the palladium oxidation using computation-guided experiments for reactions involving strong chelation control. We find that a mild external ligand could significantly accelerate the oxidation of palladium(II) to palladium(IV) for strong bidentate directing groups. The acceleration is believed to be a result of ligand stabilization of both the palladium(II) and palladium(IV) intermediates. (Figure presented.) .

Cross-coupling of remote meta -c-h bonds directed by a u-shaped template

meta-C-H arylation and methylation of 3-phenylpropanoic acid and phenolic derivatives were developed using an easily removable nitrile template. The combination of a weakly coordinating U-shaped template and mono-protected amino acid ligand was crucial fo

Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH2 at the human melanocortin-1 and -4 receptors: Histidine substitution

Systematic substitution of His6 residue using non-selective hMC4R pentapeptide agonist (Bu-His6-DPhe7-Arg8-Trp9-Gly 10-NH2) as the template led to the identification of Bu-Atcsu

Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluoro-1-indanylidene)acetamide, a potent, centrally acting muscle relaxant with antiinflammatory and analgesic activity

The design of rigid cyclic analogues derived from cinnamamide 1, (E)-N-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide, and β-methylcinnamamide 2, (E)-N-cyclopropyl-3-(3-fluorophenyl)but-2-enamide, has led to the discovery of the potent, centrally acting muscle relaxant (E)-2-(4,6-difluoro-1-indanylidene)acetamide, 17. Compound 17 also possesses potent antiinflammatory and analgesic activity. This paper describes the synthesis and the muscle relaxant, antiinflammatory, and analgesic structure-activity relationships of 17 and 67 of its analogues. Compound 17 has been taken into phase I clinical trials.

Selective cyclic peptides with melanocortin-4 receptor (MC4-R) agonist activity

Peptides cyclized via disulfide or lactam bridges having melanocortin-4 receptor (MC4-R) agonist activity useful for treatment of obesity.