Syntheses of tetrahydro-β-carbolines via a tandem hydroformylation-Pictet- Spengler reaction. Scope and limitations

被引:15
作者
Bondzic, Bojan P. [1 ]
Eilbracht, Peter [1 ]
机构
[1] Tech Univ, Fachbereich Chem, D-44227 Dortmund, Germany
关键词
D O I
10.1039/b809157a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel one-pot synthesis of tetrahydro-beta-carboline systems via tandem hydroformylation-Pictet-Spengler reaction starting from olefins and aryl ethylamines is described. This tandem procedure allows fast and convenient synthesis of various substituted tetrahydro-beta-carbolines.
引用
收藏
页码:4059 / 4063
页数:5
相关论文
共 38 条
[1]   ''Pictet-Spengler-like'' synthesis of tetrahydro-beta-carbolines under hydrolytic conditions. Direct use of azalactones as phenylacetaldehyde equivalents [J].
Audia, JE ;
Droste, JJ ;
Nissen, JS ;
Murdoch, GL ;
Evrard, DA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7937-7939
[2]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[3]   β-phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 2004, 21 (03) :395-424
[4]   A versatile synthesis of pyrazolo [3,4-c] isoquinoline derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl aldehydes:: the effect of the heterocycle on the reaction pathways [J].
Bogza, SL ;
Kobrakov, KI ;
Malienko, AA ;
Perepichka, IF ;
Sujkov, SY ;
Bryce, MR ;
Lyubchik, SB ;
Batsanov, AS ;
Bogdan, NM .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) :932-940
[5]   Hydroformylation of alkenes: An industrial view of the status and importance [J].
Bohnen, HW ;
Cornils, B .
ADVANCES IN CATALYSIS, VOL 47, 2002, 47 :1-64
[6]  
Brown R. T, 1983, INDOLES 4
[7]   Tandem metal- and organocatalysis in sequential hydroformylation and enantioselective aldol reactions [J].
Chercheja, Serghei ;
Eilbracht, Peter .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) :1897-1905
[8]   Regioselectivity of Pictet-Spengler cyclization: synthesis of halotetrahydroisoquinolines [J].
Cho, SD ;
Song, SY ;
Hur, EJ ;
Chen, M ;
Joo, WH ;
Falck, JR ;
Yoon, YJ ;
Shin, DS .
TETRAHEDRON LETTERS, 2001, 42 (36) :6251-6253
[9]   Chiral auxiliary mediated Pictet-Spengler reactions - Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine. [J].
Comins, DL ;
Thakker, PM ;
Baevsky, MF ;
Badawi, MM .
TETRAHEDRON, 1997, 53 (48) :16327-16340
[10]   Bulk and fine chemicals via aqueous biphasic catalysis [J].
Cornils, B .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) :1-10