Tandem hydroformylation-hydrazone formation-Fischer indole synthesis: a novel approach to tryptamides

被引:45
作者
Schmidt, AM [1 ]
Eilbracht, P [1 ]
机构
[1] Univ Dortmund, Fachbereich Chem, D-44227 Dortmund, Germany
关键词
D O I
10.1039/b503396a
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 indole systems via tandem hydroformylation-hydrazone formation-Fischer indolization starting from allylic amides and aryl hydrazines is described. This tandem procedure directly leads to biologically interesting tryptamides and analogues.
引用
收藏
页码:2333 / 2343
页数:11
相关论文
共 50 条
[41]   One-pot tandem enantioselective hydrogenation- hydroformylation synthesis of cyclic α-amino acids [J].
Teoh, E ;
Campi, EM ;
Jackson, WR ;
Robinson, AJ .
NEW JOURNAL OF CHEMISTRY, 2003, 27 (02) :387-394
[42]   A highly enantioselective synthesis of cyclic α-amino acids involving a one-pot, single catalyst, tandem hydrogenation-hydroformylation sequence [J].
Teoh, E ;
Campi, EM ;
Jackson, WR ;
Robinson, AJ .
CHEMICAL COMMUNICATIONS, 2002, (09) :978-979
[43]   CATALYTIC SYNTHESIS OF 3-SUBSTITUTED INDOLES USING CO AS BUILDING BLOCK AND SUPPORTED RHODIUM AS CATALYST [J].
UCCIANI, E ;
BONFAND, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :82-83
[44]  
van Leeuwen P. W. N. M, 2000, RHODIUM CATALYZED HY
[45]   Selective hydroformylation of N-allylacetamide in an inverted aqueous two-phase catalytic system, enabling a short synthesis of melatonin [J].
Verspui, G ;
Elbertse, G ;
Sheldon, FA ;
Hacking, MAPJ ;
Sheldon, RA .
CHEMICAL COMMUNICATIONS, 2000, (15) :1363-1364
[46]   A palladium-catalyzed method for the preparation of indoles via the Fischer indole synthesis [J].
Wagaw, S ;
Yang, BH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (44) :10251-10263
[47]   A palladium-catalyzed strategy for the preparation of indoles: A novel entry into the Fischer indole synthesis [J].
Wagaw, S ;
Yang, BH ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6621-6622
[48]  
Wittmann K, 2001, CHEM-EUR J, V7, P4584, DOI 10.1002/1521-3765(20011105)7:21<4584::AID-CHEM4584>3.0.CO
[49]  
2-P
[50]   Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides [J].
Wolter, M ;
Klapars, A ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (23) :3803-3805