Direct syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines and 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines via hydroamination of enol carbamates

作者: José Crecente-Campo , M. Pilar Vázquez-Tato , Julio A. Seijas

DOI: 10.1016/J.TET.2009.01.098

关键词:

摘要: Abstract An efficient and simple procedure for the syntheses of 4-aryl-1,2,3,4-tetrahydroisoquinolines 1-aryl-2,3,4,5-tetrahydro-3-benzoazepines has been developed. The approach uses easily available starting materials requires just three steps. hydroamination an enol carbamate is key step. This general direct method applied to total synthesis natural alkaloid cherylline biologically active 3-benzoazepines as well.

参考文章(58)
J. J. Hansen, P. Krogsgaard-Larsen, Excitatory amino acid receptors : design of agonists and antagonists E. Horwood. ,(1992)
HIROSHI HARA, RYUICHI SHIRAI, OSAMU HOSHINO, BUNSUKE UMEZAWA, Studies on Tetrahydroisoquinolines. XXV. A Synthesis of 4-Aryl-1,2,3,4-tetrahydroisoquinolines ; Total Synthesis of (±)-Cherylline Chemical & Pharmaceutical Bulletin. ,vol. 33, pp. 3107- 3112 ,(1985) , 10.1248/CPB.33.3107
Zygmunt L. Kruk, Christopher J. Pycock, Neurotransmitters and drugs ,(1979)
E. Zara-Kaczian, L. Gyorgy, Gyula Deak, A. Seregi, M. Doda, Synthesis and pharmacological evaluation of some new tetrahydroisoquinoline derivatives inhibiting dopamine uptake and/or possessing a dopaminomimetic property. Journal of Medicinal Chemistry. ,vol. 29, pp. 1189- 1195 ,(1986) , 10.1021/JM00157A012
S Chandrasekhar, N.Ramakrishna Reddy, M.Venkat Reddy, B Jagannadh, A Nagaraju, A Ravi Sankar, A.C Kunwar, Highly efficient synthesis of 3-alkyl/aryl-4-aryl-1,2,3,4-tetrahydroisoquinolines from N,N-dibenzylaminols Tetrahedron Letters. ,vol. 43, pp. 1885- 1888 ,(2002) , 10.1016/S0040-4039(02)00130-2
JUN'ICHI KATAKAWA, HIDEAKI YOSHIMATSU, MORIHIRO YOSHIDA, YONG ZHANG, HIROSHI IRIE, HARUAKI YAJIMA, Synthesis of Amaryllidaceae alkaloids, (±)-cherylline and (±)-latifine Chemical & Pharmaceutical Bulletin. ,vol. 36, pp. 3928- 3932 ,(1988) , 10.1248/CPB.36.3928
Julio A. Seijas, M.Pilar Vázquez-Tato, César Entenza, M. Montserrat Martínez, M.Gabriela Ònega, Susana Veiga, Synthesis of β-phenylethylamines from styrene derivatives Tetrahedron Letters. ,vol. 39, pp. 5073- 5076 ,(1998) , 10.1016/S0040-4039(98)00907-1
Atanas P. Venkov, Daniel M. Vodenicharov, A New Synthesis of 1,2,3,4-Tetrahydro-2-methyl-4-phenylisoquinolines Synthesis. ,vol. 1990, pp. 253- 255 ,(1990) , 10.1055/S-1990-26846