472986-90-6Relevant articles and documents
Palladium-mediated total synthesis of 2-styrylbenzoic acids: A general route to 2-azachrysenes
Pampín, Carme,Estévez, Juan C,Castedo, Luis,Estévez, Ramón J
, p. 4551 - 4553 (2002)
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
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)
Pampín, M. Carme,Estévez, Juan C.,Estévez, Ramón J.,Maestro, Miguel,Castedo, Luis
, p. 7231 - 7243 (2007/10/03)
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.
