Pd-catalyzed cyclization of 1-allyl-2-indolecarboxamides by intramolecular amidation of unactivated ethylenic bond

被引:47
作者
Abbiati, G
Beccalli, E
Broggini, G
Martinelli, M
Paladino, G
机构
[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
[2] Univ Milan, Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy
关键词
cyclizations; fused-ring systems; indoles; palladium; domino reactions;
D O I
10.1055/s-2005-922788
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The intramolecular Pd(II)-mediated cyclization of 1-allyl-2-indolecarboxamides leads to pyrazino[1,2-a]indoles throng the conversion of the olefinic C-H bond into a C-N bond by reaction with an amide group. When operating on the allylamide, a domino process was observed with a double C-H functionalization.
引用
收藏
页码:73 / 76
页数:4
相关论文
共 51 条
[1]   Intramolecular cyclization of δ-iminoacetylenes:: A new entry to pyrazino[1,2-a]indoles [J].
Abbiati, G ;
Arcadi, A ;
Bellinazzi, A ;
Beccalli, E ;
Rossi, E ;
Zanzola, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4088-4095
[2]   Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives [J].
Abbiati, G ;
Beccalli, EM ;
Broggini, G ;
Zoni, C .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7625-7628
[3]  
ABBIATI G, IN PRESS SYNTHESIS
[4]   Palladium-catalyzed ring-forming aminoacetoxylation of alkenes [J].
Alexanian, EJ ;
Lee, C ;
Sorensen, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7690-7691
[5]   PALLADIUM-CATALYZED TANDEM CYCLIZATION OF 4,6-DIENE AND 5,7-DIENE AMIDES - A NEW ROUTE TOWARD THE PYRROLIZIDINE AND INDOLIZIDINE ALKALOIDS [J].
ANDERSSON, PG ;
BACKVALL, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (22) :8696-8698
[6]  
BACKVALL JE, 1990, J AM CHEM SOC, V112, P3683
[7]   Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].
Bar, GLJ ;
Lloyd-Jones, GC ;
Booker-Milburn, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309
[8]   Regioselective formation of six- and seven-membered ring by intramolecular Pd-catalyzed amination of N-allyl-anthranilamides [J].
Beccalli, EM ;
Broggini, G ;
Paladino, G ;
Penoni, A ;
Zoni, C .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5627-5630
[9]   Uncommon intramolecular palladium-catalyzed cyclization of indole derivatives [J].
Beccalli, EM ;
Broggini, G .
TETRAHEDRON LETTERS, 2003, 44 (09) :1919-1921
[10]   Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones [J].
Beccalli, EM ;
Broggini, G ;
Marchesini, A ;
Rossi, E .
TETRAHEDRON, 2002, 58 (33) :6673-6678