40141-98-8

Upstream product

• 854255-47-3 5-methyl-6-oxo-5,6-dihydro-[1,3]dioxolo[4,5-j]phenanthridine-4-carboxylic acid 
• 40141-79-5 2-bromo-N-methyl-4,5-methylenedioxybenzanilide 
• 138883-35-9 N-(2-iodophenyl)-N-methyl-3,4-methylenedioxybenzylamide 
• 507-79-9 tazettine 
• 201230-82-2 carbon monoxide 
• 57056-93-6 N-methyl-2-iodoaniline 
• 717903-52-1 6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl triflate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 161196-32-3 methyl o-(3',4'-methylenedioxyphenyl)phenylcarbamate 
• 161196-34-5 6-methoxy<1,3>dioxolo<4,5-j>phenanthridine 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 161196-33-4 6-chloro<1,3>dioxolo<4,5-j>phenanthridine 
• 65367-81-9 N-Methyl-8,9-methylenedioxy-phenantridinium chloride 
• 339267-17-3 6-bromo-N-phenylbenzo[d][1,3]dioxole-5-carboxamide 

Downstream Products

• 65367-81-9 N-Methyl-8,9-methylenedioxy-phenantridinium chloride 

Relevant academic research and scientific papers

Copper, Silver and Sodium Salt-Mediated Quaternization by Arylation: Syntheses of N-Heterocyclic Carbene Precursors and 6-H-Phenanthridine Derivatives

We have developed a CuII-, AgI-, and NaOTf-mediated intramolecular quaternization by arylation reactions to synthesize a variety of N-heterocyclic carbene (NHC) precursors with a benzene-fused backbone. The methodology also provides a convenient alternative route for the synthesis of 6-H-phenanthridine derivatives. A novel silver–NHC complex was prepared by treatment of Ag2O with the free carbene, which was in situ prepared from the deprotonation of a representative quinazolinonium salt.

Metal-free tandem carbene N-H insertions and C-C bond cleavages

A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage. Compared to the simple N-H insertion manipulation of diazo, this method elegantly accomplishes a tandem N-H insertion/SEAr/C-C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. This journal is

Application of phenanthridine compounds to pesticides

The invention relates to an application of phenanthridine compounds shown in general formula (1) to pesticides. Part of the compounds is used as a plant virus agent and can well inhibit the tobacco mosaic virus; when used as a bactericide, the compounds have good inhibitory activity on tomato early blight, wheat scab, potato late blight, phytophthora capsici, rape sclerotinia rot, cucumber gray mould, rice sheath blight disease, cucumber fusarium wilt, cercospora brown spot of peanut, apple ring rot, wheat sharp eyespot, corn southern leaf blight, watermelon anthracnose and rice bakanae disease; when used as an insecticide, the compounds have poisonous activity on armyworms, mosquito larvae, cotton bollworms, ostrinia nubilalis, aphids, adult mites and plutella xylostella. In the formula,when molecular nitrogen is not imine, R can represent hydrogen atoms, methyl, acetyl and benzoyl; R and R represent a hydrogen atom or an oxygen atom simultaneously; R and R can represent hydroxyl, acetoxyl, methoxyl, methyleneoxy, a fluorine atom and the hydrogen atom; R is a bromine atom or the fluorine atom; R is the hydrogen atom or vinyl. When nitrogen is imine, R doesnot represent any group; one of R and R does not represent any group, and the other can represent the hydrogen atom, methoxyl, ethyoxyl, benzyloxy and a chlorine atom; R, R, R and Rrepresent the hydrogen atom.

Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds

The synthesis of phenanthridinones via denitrogenative annulation of 1,2,3-benzotriazin-4-(3H)-ones with arynes catalysed by Ni(0)/dppm was successfully developed. A variety of phenanthridinones were prepared in good to excellent yields. Based on this method, nature product, N-methylcrinasidine, was synthesized. (Figure presented.).

Palladium-Catalyzed Direct Synthesis of Phenanthridones from Benzamides through Tandem N–H/C–H Arylation

We report a palladium-catalyzed method for the direct synthesis of phenanthridones from benzamides in a single step. Unlike previous reports, the current protocol does not need any directing groups or any harsh conditions. This methodology has a wide functional group tolerance therefore a series of phenanthridones were synthesized with a yield up to 87 %. The efficacy of this protocol was further explored by synthesizing some important naturally occurring amaryllidaceae alkaloids in a single step with very good yields.

A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls

Tricyclic biaryls are important scaffold structures in many natural products and lead compounds in drug discovery. The formation of a biaryl unit is often the key step for the synthesis of tricyclic biaryls. Despite significant progress toward the synthesis of biaryl compounds in recent years, the direct cross-coupling of two different aryl halides is still challenging and robust methods are lacking. Herein we report a direct cross-coupling of two different aryl halides in the presence of a palladium catalyst and boron ester, which provides a new and useful complementary method to synthesize tricyclic biaryls.

Facile Synthesis of Phenanthridinone Alkaloids via Suzuki–Miyaura Cross-coupling

Phenanthridinone alkaloids crinasiadine 1 and N-alkylcrinasiadines 6, 7, 8, 9, 10 have been synthesized based on palladium-catalyzed tandem C–C and C–N bond formation starting from 2-aminophenylboronic acid and 2-bromobenzoate in short steps. Related alka

Pd/Cu-Catalyzed aerobic oxidative aromatic C-H bond activation/N-dealkylative carbonylation towards the synthesis of phenanthridinones

It is important to achieve diverse functionalization of tertiary anilines due to their importance in biological molecules, pharmaceutical, functional materials, and ligands. A straightforward Pd/Cu-catalyzed oxidative C-H bond activation/N-dealkylative carbonylation of tertiary [1,1′-biphenyl]-2-anilines towards the synthesis of various biologically important phenanthridin-6(5H)-ones has been developed. A wide range of functional groups are well tolerated in this transformation. Moreover, O2 is utilized as the terminal oxidant to promote the oxidative carbonylation process.

Rapid synthesis of ismine, a bioactive amaryllidaceae alkaloid

Ismine (6-[2-(methylamino)phenyl]-1,3-benzodioxole-5-methanol, 1), a biologically active alkaloid, has been synthesised by a rapid and simple four-step sequence. This synthesis involved a consecutive aryl-aryl and N-aryl coupling, leading to a phenanthridine derivative in a one-pot sequence, which employed a palladium catalyst and trifurylphosphine as the ligand. This synthesis gave an overall yield of 23%.