Pd-catalyzed intramolecular cyclization of pyrrolo-2-carboxamides: regiodivergent routes to pyrrolo-pyrazines and pyrrolo-pyridines

被引:41
作者
Beccalli, EM
Broggini, G
Martinelli, M
Paladino, G
机构
[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
[2] Univ Milan, Fac Farm, Ist Chim Organ A Marchesini, I-20133 Milan, Italy
[3] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
关键词
amination; fused-pyrrole system; cyclization reactions; palladium; regioselectivity;
D O I
10.1016/j.tet.2004.11.066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of N-alkyl-N-allyl-pyrrolo-2-carboxamides with catalytic amounts of palladium derivatives gave regioselectively intramolecular cyclizations to generate bicyclic pyrrolo-fused structures. Pyrrolo[1,2-a]pyrazin-1-ones were achieved in high yields by an amination reaction, while pyrrolo [2,3-c]pyridin-7-ones and pyrrolo[3,2-c]pyridin-4-ones were obtained by an oxidative coupling process. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1077 / 1082
页数:6
相关论文
共 32 条
[1]   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
[2]   Palladium-mediated approach to dibenzo[b,e][1,4]diazepines and benzopyrido-analogues.: An efficient synthesis of tarpane [J].
Beccalli, EM ;
Broggini, G ;
Paladino, G ;
Zoni, C .
TETRAHEDRON, 2005, 61 (01) :61-68
[3]   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
[4]   Uncommon intramolecular palladium-catalyzed cyclization of indole derivatives [J].
Beccalli, EM ;
Broggini, G .
TETRAHEDRON LETTERS, 2003, 44 (09) :1919-1921
[5]   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
[6]   A new synthesis of staurosporinone [J].
Beccalli, EM ;
Gelmi, ML ;
Marchesini, A .
TETRAHEDRON, 1998, 54 (24) :6909-6918
[7]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[8]   Advances and adventures in amination reactions of olefins and alkynes [J].
Beller, M ;
Breindl, C ;
Eichberger, M ;
Hartung, CG ;
Seayad, J ;
Thiel, OR ;
Tillack, A ;
Trauthwein, H .
SYNLETT, 2002, (10) :1579-1594
[9]   Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(cyclohexylidene)amines [J].
DeKimpe, N ;
Keppens, M .
TETRAHEDRON, 1996, 52 (10) :3705-3718
[10]   STUDIES ON SUGAR NITRO-OLEFINS .7. SYNTHESIS OF 3-(ALDITOL-1-YL)-1,2,3,5,6,7-HEXAHYDRO-INDOL-4-ONES AND -1,5,6,7-TETRAHYDRO-INDOL-4-ONES - X-RAY MOLECULAR-STRUCTURE OF (3S)-3-(1,2,3,4,5-PENTA-O-ACETYL-D-GALACTO-PENTITOL-1-YL)-1,2,3,5,6,7-HEXAHYDROINDOL-4-ONE [J].
DIANEZ, MJ ;
GALAN, J ;
GOMEZSANCHEZ, A ;
LOPEZCASTRO, A ;
RICO, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :581-588