Diels-Alder Reactions of 2-Vinylindoles with Cyclic Dienophiles: Synthesis of [c]-Annulated Tetrahydrocarbazoles

被引:18
作者
Pirovano, Valentina [1 ]
Abbiati, Giorgio [1 ]
Dell'Acqua, Monica [1 ]
Facoetti, Diego [1 ]
Giordano, Mara [1 ]
Rossi, Elisabetta [1 ]
机构
[1] Univ Milan, Dipartimento Sci Farmaceut, Sez Chim Gen & Organ Alessandro Marchesi, I-20133 Milan, Italy
关键词
Diels-Alder reaction; heterocycles; polycycles; Lewis acids; indoles; FISCHER INDOLE; CARBAZOLE ALKALOIDS; CYCLOADDITION; VINYLINDOLES; GLYCOMAURROL;
D O I
10.1055/s-0032-1317588
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diels-Alder reactions of 2-vinylindoles with cyclic carbo- and heterodienophiles, in the presence of suitable Lewis acids, led to uncommon [c]-carbo- and furoannulated tetrahydrocarbazoles. The obtained compounds encompass a carbonyl group in an angular position, suitable for further transformations, and represent useful intermediates for the synthesis of more complex structures.
引用
收藏
页码:2913 / 2918
页数:6
相关论文
共 43 条
[1]   Diels-Alder reactions of 2-vinylindoles with open-chain C=C dienophiles [J].
Abbiati, Giorgio ;
Canevari, Valentina ;
Facoetti, Diego ;
Rossi, Elisabetta .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (03) :517-525
[2]  
AKGUN E, 1989, J HETEROCYCLIC CHEM, V26, P1869
[3]   Free radical cyclizations in alkaloid total synthesis: (+/-)-21-oxogelsemine and (+/-)-gelsemine [J].
Atarashi, S ;
Choi, JK ;
Ha, DC ;
Hart, DJ ;
Kuzmich, D ;
Lee, CS ;
Ramesh, S ;
Wu, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (27) :6226-6241
[4]   Synthesis of Pyrrole and Carbazole Alkaloids [J].
Bauer, Ingmar ;
Knoelker, Hans-Joachim .
ALKALOID SYNTHESIS, 2012, 309 :203-253
[5]   Investigations into the Regioselectivity of Fischer Indole and Friedlander Quinoline Syntheses with Octahydroisobenzofuran and Octahydroisoindole Derivatives [J].
Bender, Matthias ;
Christoffers, Jens .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2011, 66 (12) :1209-1218
[6]   Highly enantioselective [4+2]cycloaddition reactions catalyzed by a chiral N-methyl-oxazaborolidinium cation [J].
Canales, Eda ;
Corey, E. J. .
ORGANIC LETTERS, 2008, 10 (15) :3271-3273
[7]   Organocatalytic Multiple Cascade Reactions: A New Strategy for the Construction of Enantioenriched Tetrahydrocarbazoles [J].
Cao, Yi-Ju ;
Cheng, Hong-Gang ;
Lu, Liang-Qiu ;
Zhang, Ji-Ji ;
Cheng, Ying ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (04) :617-623
[8]   Synthesis of new 2-vinylation products of indole via a michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles [J].
Cavdar, Huseyin ;
Saracoglu, Nurullah .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7793-7799
[9]   SYNTHETIC STUDIES ON NITROGEN-CONTAINING FUSED-HETEROCYCLIC COMPOUNDS BASED ON THERMAL ELECTROCYCLIC REACTIONS OF 6π-ELECTRON AND AZA 6π-ELECTRON SYSTEMS [J].
Choshi, Tominari ;
Hibino, Satoshi .
HETEROCYCLES, 2011, 83 (06) :1205-1239
[10]   An example of regioselective Fischer indole annulation [J].
Christoffers, J .
SYNLETT, 2006, (02) :318-320