38491-36-0

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 40138-16-7 2-formylbenzene boronic acid 
• 10365-98-7 3-methoxyphenylboronic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 82632-38-0 N-tert-butyl-1-(2-methoxyphenyl)methanimine 
• 579-72-6 2-(dimethylamino)benzaldehyde 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 93867-72-2 7-(3-Methoxy-phenyl)-tropiliden 
• 309254-43-1 (3'-methoxy-[1,1'-biphenyl]-2-yl)methanol 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 135-02-4 ortho-anisaldehyde 
• 95149-16-9 tris-(3-methoxy-phenyl)-bismuthane 
• 26260-02-6 2-iodobenzaldehyde 

Downstream Products

• 1587718-60-2 1-(3'-methoxy-[1,1'-biphenyl]-2-yl)-3-phenylprop-2-yn-1-one 
• 41001-28-9 9-methoxyphenanthridine 
• 1194718-79-0 7-methoxyphenanthridine 
• 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 
• 834-99-1 1-methoxyphenanthrene 

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

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.

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.

Efficient Oxidative Coupling of Arenes via Electrochemical Regeneration of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under Mild Reaction Conditions

The intramolecular dehydrogenative carbon-carbon bond formation of aromatic rings in the presence of catalytic amounts of an oxidising agent is herein described. The oxidative coupling is realised under indirect anodic conditions, utilising 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as an efficient redox mediator under acidic conditions. In comparison, for the stoichiometric oxidative coupling reaction of hexakis(4-tert-butylphenyl)benzene on a 1.0 gram scale, 1.56 g of DDQ were applied, whereas in the present indirect electrochemical version, only 15 mg of DDQ were needed, resulting in significantly easier purifications of the products. The reaction proceeds smoothly using a variety of polyaromatics including terphenyl, quaterphenyl and heptaphenyl derivatives to give polyphenylenes in excellent yields and current efficiencies. A detailed optimisation study, investigations on the electrochemical behaviour of the redox mediator and synthetic applications of the method are discussed. (Figure presented.).

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.