20927-47-3

Upstream product

• 80592-32-1 2-formamido-4-chlorobiphenyl 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 29608-78-4 4-chloro-2-nitro-1,1'-biphenyl 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 588-07-8 3-Chloroacetanilide 
• 108-42-9 3-chloro-aniline 
• 18982-54-2 o-bromobenzyl alcohol 
• 7154-66-7 2-bromobenzoic acid chloride 
• 88-65-3 2-bromobenzoic-acid 
• 66569-06-0 2-bromo-N-(4-chlorophenyl)benzamide 
• 6828-35-9 5-chloro-2-iodoaniline 
• 2446-83-5 di-isopropyl azodicarboxylate 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Method for synthesizing phenanthridone compound

The invention discloses a method for synthesizing a phenanthridone compound. The method comprises the following steps of: adding an N-hydrocarbon acyloxy amide compound, a transition metal catalyst, acocatalyst and an organic solvent into a reaction container in a nitrogen atmosphere, reacting at 0-40 DEG C for 1-12 hours, and separating and purifying a reaction product to obtain the phenanthridone compound. The method for synthesizing the phenanthridone compound, disclosed by the invention, has the following advantages that: 1, the reaction conditions are mild; 2, less catalyst is used; 3, aligand and an acid-base additive are not needed, the substrate application range is wide, and the method can be compatible with various functional groups such as halogen. 4, the operation is simple;5, the product selectivity is high.

Organocatalyst in Direct C(sp2)-H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed Inter-/Intra-molecular C-H Bond Activation

This article describes the identification of 1-(2-hydroxyethyl)-piperazine as a new, cost-effective, highly efficient organocatalyst, which promotes both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in the presence of potassium tert-butoxide. While the inter-molecular C-H arylation of unactivated benzenes with aryl halides (Ar-X; X = I, Br, Cl) toward biaryl syntheses underwent smoothly in the presence of only 10 mol percent organocatalyst, the intra-molecular C-H arylation catalytic system composed of 40 mol percent each of the catalyst and the additive (4-dimethylaminopyridine (DMAP)). The novel catalyst was also able to perform both inter- A nd intra-molecular direct arylations simultaneously in a single pot. The mechanistic studies confirmed the involvement of aryl radical anions and proceeded via a single-electron-transfer (SET) mechanism. The large substrate scope, high functional group tolerance, competition experiments, gram-scale synthesis, and kinetic studies further highlight the importance and versatile nature of the methodology as well as the compatibility of the new catalyst. To the best of our knowledge, this is the first report on any organocatalyst that reported detailed investigations of both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in a single representation.

Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2

An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.

Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H cross-dehydrogenative coupling (CDC)

A Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H bond cross-dehydrogenative coupling of 2-aryloxybenzaldehydes is described. A variety of substituted xanthone derivatives are synthesized in moderate to excellent yields. Reaction can also be extended to the synthesis of 9H-thioxanthen-9-one 10,10-dioxide and phenanthridin-6(5H)-ones, respectively.

Metal-Oxidant-Free Cobalt-Catalyzed C(sp2)-H Carbonylation of ortho-Arylanilines: An Approach toward Free (NH)-Phenanthridinones

A traceless directing group assisted Co-catalyzed C(sp2)-H carbonylation of ortho-arylanilines for the synthesis of free (NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total synthesis of PARP inhibitor PJ-34. Furthermore, the kinetic isotopic effect experiments reveal the C-H bond cleavage probably occurred in the rate-determining step.

Phenanthridine ketone compounds

The invention relates to a synthetic method of phenanthridine ketone compounds, which comprises the steps of taking and adding o-haloaromaticamine and aryl methyl alcohol (or arylamine and o-haloaryl methyl alcohol) as well as a ruthenium catalyst, palladium chloride, azacyclo-imidazolium salt and alkali into an organic solvent, heating at the protection of N2 gas, and generating the phenanthridine ketone compounds by one step through a hydrogen transfer reaction and a carbon-hydrogen bond activation reaction, so as to provide a practical method for synthesizing substituted phenanthridine ketone derivatives with biological activity; the method has the advantages that the operation is simple, and a reaction substrate is cheap, wide in range and high in yield, and has important application value.

Palladium-Catalyzed C-H Activation and Cyclization of Anilides with 2-Iodoacetates and 2-Iodobenzoates: An Efficient Method toward Oxindoles and Phenanthridones

A concise approach to the synthesis of oxindoles and phenanthridones from anilides is described. In the presence of catalytic amount of Pd(OAc)2, 2-iodoacetates and 2-iodobenzoates can be used to functionalize ortho C-H bond of anilides, which subsequently undergo intramolecular cyclization to give the products. A possible reaction mechanism that involves a PdII/PdIV catalytic cycle is proposed with the support of detailed mechanistic studies.

Transition-metal-free synthesis of phenanthridinones from biaryl-2-oxamic acid under radical conditions

Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products. (Chemical Equation Presented).

Synthesis of Phenanthridin-6(5 H)-ones via Copper-Catalyzed Cyclization of 2-Phenylbenzamides

Synthesis of phenanthridin-6(5H)-ones was achieved via copper-catalyzed cyclization of 2-phenylbenzamides using air as the oxidant and KOt-Bu as the base. It was discovered that, besides Ph3P, other ligands such as 1,10-phenanthroline, TMEDA as well as l-proline could also be used as the ligand to effect the transformation. Georg Thieme Verlag Stuttgart. New York.

Synthesis of phenanthridinones via palladium-catalyzed C(sp2)-H aminocarbonylation of unprotected o-arylanilines

An efficient synthesis of free (NH)-phenanthridinones through Pd-catalyzed C(sp2)-H aminocarbonylation of unprotected o-arylanilines under an atmospheric pressure of CO has been developed. Some ortho heteroarene substituted anilines as well as