174518-83-3

Upstream product

• 10385-36-1 2,3,4-trimethoxybromobenzene 

Downstream Products

• 624746-05-0 2-[2-(5-bromo-2,3,4-trimethoxyphenyl)vinyl]isoindoline-1,3-dione 
• 624746-06-1 2-{2-[2'-(2,2-dibromovinyl)-4,5,6-trimethoxybiphenyl-3-yl]ethyl}isoindoline-1,3-dione 
• 624745-94-4 2-{2-[2'-(bromoethynyl)-4,5,6-trimethoxybiphenyl-3-yl]ethyl}isoindoline-1,3-dione 
• 624745-93-3 5'-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl]-2',3',4'-trimethoxybiphenyl-2-carbaldehyde 
• 624745-92-2 2-[2-(5-bromo-2,3,4-trimethoxyphenyl)ethyl]isoindoline-1,3-dione 

Relevant academic research and scientific papers

Synthesis of phenanthrenes and polycyclic heteroarenes by transition-metal catalyzed cycloisomerization reactions

Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl2, AuCl, AuCl3, GaCl3 or InCl3 in toluene. This 6-endo-dig cyclization likely proceeds through initial π-complexation of the alkyne unit followed by interception of the resulting η2-metal species by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product. Moreover, it is readily extended to the heterocyclic series as exemplified by the preparation of benzoindoles, benzocarbazoles, naphthothiophenes, as well as bridgehead nitrogen heterocycles such as pyrrolo[1,2-a]quinolines. Depending on the chosen catalyst, biaryls bearing halo-alkyne units can either be converted into the corresponding 10-halo-phenanthrenes or into the isomeric 9-halo-phenanthrenes; in the latter case, the concomitant 1,2-halide shift is best explained by assuming a metal vinylidene species as the reactive intermediate. The scope of this novel method for the preparation of polycyclic arenes is illustrated by the total synthesis of a series of polyoxygenated phenanthrenes that are close relatives of the anticancer agent combretastatin A-4, as well as by the total synthesis of the aporphine alkaloid O-methyl-dehydroisopiline and its naturally occurring symmetrical dimer.

Concise total synthesis of the aporphine alkaloid 7,7'-bisdehydro-O-methylisopiline by an InCl3 mediated cycloisomerization reaction.

A novel InCl3 mediated cycloisomerization reaction leading to 10-halophenanthrene derivatives constitutes the key step of the first total syntheses of O-methyldehydroisopiline 10 and 7,7'-bisdehydro-O-methylisopiline 11, two prototype members of the aporp

Iodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane

A convenient method for selective mono- and diiodination of alkyl aryl ethers by mercury(II) oxide-iodine reagent in dichloromethane is reported.