Tetrahedron

Heck-mediated synthesis and photochemically induced cyclization of [2-(2-styrylphenyl) ethyl] carbamic acid ethyl esters and 2-styryl-benzoic acid methyl esters: total …

…, JC Estévez, RJ Estévez, M Maestro, L Castedo

Index: Pampin, M. Carme; Estevez, Juan C.; Estevez, Ramon J.; Maestro, Miguel; Castedo, Luis Tetrahedron, 2003 , vol. 59, # 36 p. 7231 - 7243

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Citation Number: 25

Abstract

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 ...