Synthesis of Azocino[5,4‐b]indoles via Gold‐Catalyzed Intramolecular Alkyne Hydroarylation

作者: Vsevolod A. Peshkov , Olga P. Pereshivko , Erik V. Van der Eycken

DOI: 10.1002/ADSC.201200305

关键词:

摘要: An efficient procedure for the synthesis of azocino[5,4-b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation propargylic amides derived from various tryptamines and 3-substituted 2-propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior our previously described mercury(II) catalyst, hence substrate scope process significantly expanded.

参考文章(56)
Takushi KURIHARA, Yasuhiko SAKAMOTO, Masato TAKAI, Kaori OHUCHI, Shinya HARUSAWA, Ryuji YONEDA, Meisenheimer Rearrangement of Azetopyridoindoles. III. Synthesis of 3,6-Epoxyhexahydroazocino(5,4-b) indoles. Chemical & Pharmaceutical Bulletin. ,vol. 41, pp. 1221- 1225 ,(1993) , 10.1248/CPB.41.1221
Charles C. J. Loh, Jan Badorrek, Gerhard Raabe, Dieter Enders, Merging organocatalysis and gold catalysis: enantioselective synthesis of tetracyclic indole derivatives through a sequential double Friedel-Crafts type reaction. Chemistry: A European Journal. ,vol. 17, pp. 13409- 13414 ,(2011) , 10.1002/CHEM.201102793
Lionel Moisan, Pierre Thuéry, Marc Nicolas, Eric Doris, Bernard Rousseau, Formal Synthesis of (+)‐Catharanthine Angewandte Chemie. ,vol. 45, pp. 5334- 5336 ,(2006) , 10.1002/ANIE.200601307
Mark Mascal, Kyle V. Modes, Asuman Durmus, Concise Photochemical Synthesis of the Antimalarial Indole Alkaloid Decursivine Angewandte Chemie. ,vol. 50, pp. 4445- 4446 ,(2011) , 10.1002/ANIE.201006423
Catalina Ferrer, Ana Escribano-Cuesta, Antonio M. Echavarren, Synthesis of the tetracyclic core skeleton of the lundurines by a gold-catalyzed cyclization Tetrahedron. ,vol. 65, pp. 9015- 9020 ,(2009) , 10.1016/J.TET.2009.08.067
Barry M. Trost, Stephen A. Godleski, Jean P. Genet, A total synthesis of racemic and optically active ibogamine. Utilization and mechanism of a new silver ion assisted palladium catalyzed cyclization Journal of the American Chemical Society. ,vol. 100, pp. 3930- 3931 ,(1978) , 10.1021/JA00480A047
Kurt Freter, Darstellung von Azepino[4.5‐b]indolen European Journal of Organic Chemistry. ,vol. 721, pp. 101- 104 ,(1969) , 10.1002/JLAC.19697210114
Antonio Arcadi, Alternative synthetic methods through new developments in catalysis by gold. Chemical Reviews. ,vol. 108, pp. 3266- 3325 ,(2008) , 10.1021/CR068435D