472986-90-6

Upstream product

• 100-42-5 styrene 
• 173043-61-3 2-iodo-4,5-dimethoxybenzoic acid methyl ester 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 53012-84-3 2-formyl-4,5-dimethoxybenzoic acid methyl ester 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 93-07-2 Veratric acid 

Downstream Products

• 56156-96-8 6,7-dimethoxy-3-phenyl-1H-isochromen-1-one 
• 76352-39-1 6,7-dimethoxy-2-methyl-3-phenyl-1(2H)-isoquinolone 

Relevant academic research and scientific papers

Palladium-mediated total synthesis of 2-styrylbenzoic acids: A general route to 2-azachrysenes

We describe a new total synthesis of 2-styrylbenzoic acids by Heck coupling of methyl o-iodobenzoates to styrenes. Additionally, in the first general synthesis of naphtho[2,1-f]isoquinolines, these acids were transformed into phenanthrenoic acids and then

Preparation of dihydroxy polycyclic aromatic hydrocarbons and activities of two dioxygenases in the phenanthrene degradative pathway

Dihydroxy phenanthrene, fluoranthene, and pyrene derivatives are intermediates in the bacterial catabolism of the corresponding parent polycyclic aromatic hydrocarbon (PAH). Ring-opening of the dihydroxy species followed by a series of enzyme-catalyzed re

Heck-mediated synthesis and photochemically induced cyclization of [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters and 2-styryl-benzoic acid methyl esters: Total synthesis of naphtho[2,1f]isoquinolines (2-azachrysenes)

We describe two new closely related total syntheses of naphtho[2,1-f]isoquinolines. The first synthesis consists of a Heck coupling reaction between trifluoromethanesulfonic acid 2-(2-ethoxycarbonylaminoethyl)phenyl esters and styrenes to give [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters. These compounds cyclize to give (2-phenanthren-1-yl-ethyl)carbamic acid ethyl esters, from which 2-azachrysenes can be obtained in a three-step sequence. The second synthesis includes a new total synthesis of 2-styrylbenzoic acid methyl esters by Heck coupling of methyl o-iodobenzoates to styrenes, followed by the transformation of the resulting benzoic acid derivatives into phenanthrene-1-carboxylic acid methyl esters and then into the target compounds by a six-step sequence including a Bischler-Napieralski cyclization.

Synthesis of 3-substituted isocoumarins through acyloxypalladation of o-alkenylbenzoic acids

Cyclization of o-alkenylbenzoic acids in the presence of Pd catalyst and benzoquinone led to 3-substituted isocoumarins in high yield. The isocoumarins obtained were converted to isoquinolones by treatment with primary amines.