27353-44-2

Usage

InChI:InChI=1/C13H8ClNO/c14-8-5-6-12-11(7-8)9-3-1-2-4-10(9)13(16)15-12/h1-7H,(H,15,16)

Upstream product

• 1015-89-0 6(5H)-phenanthridinone 
• 609-65-4 o-chlorobenzoyl chloride 
• 1238333-76-0 5’-chloro-2’-fluoro-[1,1’-biphenyl]-2-carbonitrile 
• 486-25-9 9-fluorenone 
• 2157-52-0 9-fluorenone oxime 
• 313268-48-3 2-iodo-N-(4-chlorophenyl)benzamide 
• 106-47-8 4-chloro-aniline 
• 124-38-9 carbon dioxide 
• 73006-78-7 5-chloro[1,1'-biphenyl]-2-amine 
• 873-38-1 4-chloro-2-bromoaniline 
• 98-80-6 phenylboronic acid 
• 2446-83-5 di-isopropyl azodicarboxylate 
• 1609211-26-8 N-(5-chloro-[1,1′-biphenyl]-2-yl)picolinamide 
• 63069-48-7 p-chloro-o-iodoaniline 

Downstream Products

• 54960-76-8 2-chloro-5-methylphenanthridin-6(5H)-one 
• 1322074-84-9 2-chloro-N-[4-methylphenyl]sulfonyl-5,6-dihydrophenanthridine 
• 1322074-85-0 2-chloro-N-[2-nitrophenyl]sulfonyl-5,6-dihydrophenanthridine 
• 1322074-88-3 2-chloro-4-[(4-methylphenyl)sulfonyl]phenanthridine 
• 1322074-89-4 2-chloro-4-[(2-nitrophenyl)sulfonyl]phenanthridine 
• 38052-81-2 2.6-Dichlor-phenanthridin 

Relevant academic research and scientific papers

Photoinduced Annulation of N-Phenylbenzamides for the Synthesis of Phenanthridin-6(5H)-Ones

A general concise method for the synthesis phenanthridin-6(5H)-ones via photoinduced intramolecular annulation of N-phenylbenzamides was developed. Under argon atmosphere and room temperature, phenanthridin-6(5H)-ones were obtained via irradiation N-phenylbenzamides with a 280 nm UV lamp in the presence of methanesulfonic acid in toluene. The mechanism is illustrated and believed to proceed in the order of amides tautomerization, 6π-electric cyclization, [1,5]-H shift, amide-imidine tautomerization, keto-enol tautomerism and evolution hydrogen. (Figure presented.).

Method for efficiently preparing phenanthridone and derivatives thereof without metal participation

The invention discloses a method for efficiently preparing phenanthridone and derivatives without metal participation. The preparation method comprises the step of carrying out cyclization reaction on a compound shown in a formula II under the catalysis of methyl trifluoromethanesulfonate to obtain a phenanthridone compound shown in a formula I. According to the invention, the phenanthridone compound is generated in one step by catalyzing the cyclization reaction of the o-aryl phenyl isocyanate through the trifluoromethanesulfonate, and a practical method is provided for synthesizing the substituted phenanthridone derivative with biological activity. The method is free of using any metal reagent, environmentally friendly, easy to operate, high in yield and simple and convenient in post-treatment. In addition, the substrate obtained by the method is high in designability, a compound with the required structurecan be designed and synthesized according to actual needs, and the practicability is high.

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.

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.

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.

Continuous flow photochemistry as an enabling synthetic technology: Synthesis of substituted-6(5: H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors

Methods utilizing continuous flow photochemistry, an enabling synthetic technology, have been developed for the generation of phenanthridinones via an intramolecular photochemical cyclization of 2-chlorobenzamides for the purposes of generating poly(ADP-ribose) polymerase inhibitors. Herein we report 16 examples of a single-step flow photocyclization which produces substituted phenanthridinones in yields up to 99%, while a two-step method leads directly to phenanthridinones from 2-chlorobenzoyl chlorides and anilines via a novel continuous flow amidation/photocyclization protocol. Overall, the flow photocyclization reactions typically progress in good to excellent yields, and in a superior fashion to analogous batch methods, greatly enabling the drug discovery process.

MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones

Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.

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