38491-36-0

Upstream product

• 10365-98-7 3-methoxyphenylboronic acid 
• 135-02-4 ortho-anisaldehyde 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 82632-38-0 N-tert-butyl-1-(2-methoxyphenyl)methanimine 
• 2398-37-0 3-methoxyphenyl bromide 
• 93867-72-2 7-(3-Methoxy-phenyl)-tropiliden 
• 309254-43-1 (3'-methoxy-[1,1'-biphenyl]-2-yl)methanol 
• 579-72-6 2-(dimethylamino)benzaldehyde 
• 498-66-8 norborn-2-ene 
• 529-28-2 4-iodoanisol 
• 18982-54-2 o-bromobenzyl alcohol 
• 95149-16-9 tris-(3-methoxy-phenyl)-bismuthane 
• 6630-33-7 ortho-bromobenzaldehyde 
• 26260-02-6 2-iodobenzaldehyde 

Downstream Products

• 834-99-1 1-methoxyphenanthrene 
• 41001-28-9 9-methoxyphenanthridine 
• 1194718-79-0 7-methoxyphenanthridine 
• 1587718-60-2 1-(3'-methoxy-[1,1'-biphenyl]-2-yl)-3-phenylprop-2-yn-1-one 
• 1430810-77-7 1-(3'-methoxybiphenyl-2-ylmethyl)-4-(2-methoxyphenyl)piperazine 
• 1403848-33-8 C₂₂H₁₆O 
• 1403848-39-4 2-(1,5-diphenylpenta-1,4-diyn-3-yl)-3'-methoxy-1,1'-biphenyl 

Relevant academic research and scientific papers

Electrochemical Decarboxylative Cyclization of α-Amino-Oxy Acids to Access Phenanthridine Derivatives

Phenanthridines are a class of useful heterocycles in the field of drug development. In this work, a method via electrochemical decarboxylative cyclization of α-amino-oxy acids to access phenanthridine derivatives was developed. This reaction proceeded th

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

The Trityl Cation Embedded into a [7]Helicene-Like Backbone: Preparation and Application as a Lewis Acid Catalyst

The synthesis of a helically chiral carbenium ion is reported. The new motif is essentially a trityl cation embedded into a [7]helicene-like framework. The key step in its preparation establishes the π-extended fluorenone system in one step by an unprecedented palladium-catalyzed carbonylative annulation of a 4,4′-biphenanthryl-3,3′-diyl precursor. The racemic form of the new carbon Lewis acid was found to catalyze a representative set of reactions typically promoted by the trityl cation.

Metal-Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and β-Ketosulfones

We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal-catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β-ketosulfones. Gram scale reactions further demonstrate the practicability.

Regioselectivity-Switchable Intramolecular Hydroarylation of Ynone

The switchable catalytic approach to the regioselective intramolecular hydroarylation of ynone has been developed. When ZnI2 was used as catalyst, the umpolung α-arylation of ynone was realized via an addition-elimination process of iodine ion to generate the ortho-phenanthrenequinone methide (o-PQM), which could be trapped by styrene to form benzo[f,h]chromenes through hetero-Diels-Alder reaction. While IPrAuCl/AgSbF6 was applied, however, the β-arylation of ynone took place to afford benzocycloheptene-5-ones in moderate to excellent yields. (Figure presented.).

Gold-Catalyzed Friedel–Crafts-Like Reaction of Benzylic Alcohols to Afford 1,1-Diarylalkanes

A gold-catalyzed, Friedel–Crafts-like benzylation of unactivated benzylic alcohols to form 1,1-diarylalkanes has been developed. The operationally convenient method uses only 1.3 equivalents of the electron-rich arene, employs readily available starting m

COMPOUNDS OF PHOSPHINANES AND AZAPHOSPHINANES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Compounds of formula (I) wherein: Ak1 represents an alkyl chain, X represents —(CH2)m—, —CH(R)—, —N(R)—, —CH2—N(R)—, —N(R)—CH2— or —CH2—N(R)—CH2—, m and R are as defined in the description, R1 and R2 each represent H when X represents —(CH2)m—, —CH(R)—, —N(R)—, —CH2—N(R)— or —N(R)—CH2—, or together form a bond when X represents —CH2—N(R)—CH2—, R3 represents NH2, Cy-NH2, Cy-Ak3-NH2 or piperidin-4-yl, Cy and Ak3 are as defined in the description, R4 and R5, which may be identical or different, each represent H or F, their optical isomers, and addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating conditions requiring a TAFIa inhibitor.

Facile synthesis of 1,2-dione-containing abietane analogues for the generation of human carboxylesterase inhibitors

Recently, a series of selective human carboxylesterase inhibitors have been identified based upon the tanshinones, with biologically active molecules containing a 1,2-dione group as part of a naphthoquinone core. Unfortunately, the synthesis of such compounds is complex. Here we describe a novel method for the generation of 1,2-dione containing diterpenoids using a unified approach, by which boronic acids are joined to vinyl bromo-cyclohexene derivatives via Suzuki coupling, followed by electrocyclization and oxidation to the o-phenanthroquinones. This has allowed the construction of a panel of miltirone analogues containing an array of substituents (methyl, isopropyl, fluorine, methoxy) which have been used to develop preliminary SAR with the two human carboxylesterase isoforms. As a consequence, we have synthesized highly potent inhibitors of these enzymes (Ki 15 nM), that maintain the core tanshinone scaffold. Hence, we have developed a facile and reproducible method for the synthesis of abietane analogues that have resulted in a panel of miltirone derivatives that will be useful tool compounds to assess carboxylesterase biology.

Chromium-Catalyzed, Regioselective Cross-Coupling of C-O Bonds by Using Organic Bromides as Reactants

We report a chromium-catalyzed cross-coupling of C-O bonds with widely accessible organic bromides as reactants for the preparation of ortho -arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon-Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study

The cleavage of aromatic carbon-nitrogen bonds catalyzed by transition metals is of high synthetic interest because such bonds are common in organic chemistry. However, few metal catalysts can be used to selectively break C(aryl)-N bonds in electronically neutral molecules. We report here the first low-valent, high-spin chromium-catalyzed cleavage of C(aryl)-N bonds in electronically neutral aniline derivatives at room temperature. By using simple and inexpensive chromium(II) chloride as precatalyst, accompanied by an imino auxiliary, the selective arylative and alkylative C-C coupling of C(aryl)-N bonds can be achieved. Crossover experiments indicate that a low-valent chromium species, formed in situ by reduction of CrCl2 with Grignard reagent, is responsible for the catalytic cleavage of C(aryl)-N bonds. DFT calculations show that facile insertion of the C(aryl)-N bond by chromium(0) can take place in a high-spin quintet (S = 2) ground state, whereas the lower-spin singlet (S = 0) and triplet (S = 1) states are inaccessible in energy. It was found that both donation of the sole paired d electrons in the d6 shell of high-spin chromium(0) to the antibonding orbital of the C(aryl)-N bond and the nitrogen ligating interaction to the metal center with its lone pair play important roles in the cleavage of the C(aryl)-N bond by the zerovalent chromium species.