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C–N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids†‡
S. Aravinda,Ram A. Vishwakarma
RSC Advances Pub Date : 10/23/2013 00:00:00 , DOI:10.1039/C3RA44903C
Abstract

Copper promoted N-arylation of methyl 4-amino-3-iodobenzoate with boronic acids followed by Pd-catalyzed intramolecular C–H arylation provides an efficient route to methyl carbazole-3-carboxylate derivatives. This methodology was implemented in the synthesis of naturally occurring carbazole alkaloids clausine C, clausine H, clausine L, clausenalene, glycozoline, glycozolidine, glycozolidal and sansoakamine.

Graphical abstract: C–N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids
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