Diels-Alder reactions of fused 5-, 6-and 7-membered ring 2-vinylindoles: Synthesis of annulated tetrahydrocarbazoles

被引:4
作者
Noland, Wayland E. [1 ]
Herzig, Ryan J. [1 ]
Kumar, Honnaiah Vijay [1 ]
Narina, Venkata Srinivasarao [1 ]
Elkin, Pavel K. [1 ]
Valverde, Karen I. [1 ]
Kim, Briana L. [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
Tetrahydrocarbazoles; Diels-Alder; 2-Vinylindoles; BIOMIMETIC ALKALOID SYNTHESES; SITU VINYLINDOLE SYNTHESIS; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; SUBSTITUTED TETRAHYDROCARBAZOLES; DIMETHYL ACETYLENEDICARBOXYLATE; CARBONYL-COMPOUNDS; MALEIC-ANHYDRIDE; CYCLO-ADDITIONS; ACID;
D O I
10.1016/j.tet.2017.09.025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Scaffolds of tetrahydrocarbazoles are an important class of biologically active compounds found abundant in nature. In the present investigation, functionalized polycyclic tetrahydrocarbazoles were synthesized using Diels-Alder cycloaddition between fused 5-, 6- and 7-membered ring 2-vinylindoles and various dienophiles. The dienophiles used were N-phenylmaleimides, 1,4-naphthoquinone, and dimethyl acetylenedicarboxylate (DMAD). When 1,4-naphthoquinone was used as a dienophile, the 5 -membered ring Diels-Alder adduct was obtained in the oxidized form, but this form was not observed in the case of 6- and 7-membered ring Diels-Alder adducts. The desired product yields ranged from 60-70% and the structure of final compounds were determined using 1D and 2D NMR analysis. H-1 NMR studies confirmed excellent diastereoselectivity (>99% de). Published by Elsevier Ltd.
引用
收藏
页码:6341 / 6346
页数:6
相关论文
共 56 条
[1]   Bicyclic N-hydroxyurea inhibitors of 5-lipoxygenase: Pharmacodynamic, pharmacokinetic, and in vitro metabolic studies characterizing N-hydroxy-N-(2,3-dihydro-6-(phenylmethoxy)-3-benzofuranyl)urea [J].
Adams, JL ;
Garigipati, RS ;
Sorenson, M ;
Schmidt, SJ ;
Brian, WR ;
Newton, JF ;
Tyrrell, KA ;
Garver, E ;
Yodis, LA ;
ChabotFletcher, M ;
Tzimas, M ;
Webb, EF ;
Breton, JJ ;
Griswold, DE .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (26) :5035-5046
[2]  
AKGUN E, 1985, CHIMIA, V39, P264
[3]  
[Anonymous], MED CHEM
[4]   Catalytic Asymmetric Synthesis of Chiral 2-Vinylindole Scaffolds by Friedel-Crafts Reaction [J].
Arai, Takayoshi ;
Tsuchida, Akiko ;
Miyazaki, Tomoya ;
Awata, Atsuko .
ORGANIC LETTERS, 2017, 19 (04) :758-761
[5]   SYNTHESIS OF CARBAZOLES RELATED TO CARBAZOMYCIN, HYELLAZOLE AND ELLIPTICINE [J].
BERGMAN, J ;
PELCMAN, B .
TETRAHEDRON, 1988, 44 (16) :5215-5228
[6]   Organocatalytic asymmetric Povarov reactions with 2- and 3-vinylindoles [J].
Bergonzini, Giulia ;
Gramigna, Lucia ;
Mazzanti, Andrea ;
Fochi, Mariafrancesca ;
Bernardi, Luca ;
Ricci, Alfredo .
CHEMICAL COMMUNICATIONS, 2010, 46 (02) :327-329
[7]   A DIECKMANN/RING EXPANSION APPROACH TO TETRAHYDROPYRIDO[1,2-A]INDOLES AND TETRAHYDROAZEPINO[1,2-A]INDOLES [J].
BIT, RA ;
DAVIS, PD ;
HILL, CH ;
KEECH, E ;
VESEY, DR .
TETRAHEDRON, 1991, 47 (26) :4645-4664
[8]   Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: Synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and polycitrin A [J].
Burtoloso, Antonio Carlos B. ;
Garcia, Ariel L. L. ;
Miranda, Karen C. ;
Correia, Carlos Roque D. .
SYNLETT, 2006, (18) :3145-3149
[9]   Bronsted Acid Mediated Tandem Diels-Aider/Aromatization Reactions of Vinylindoles [J].
Chen, Cai-Bao ;
Wang, Xu-Fan ;
Cao, Yi-Ju ;
Cheng, Hong-Gang ;
Xiao, Wen-Jing .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3532-3535
[10]   Synthesis and In-vitro Antitumor Activities of Some Mannich Bases of 9-Alkyl-1,2,3,4-tetrahydrocarbazole-1-ones [J].
Chen, Jing ;
Lou, Jianshu ;
Liu, Tao ;
Wu, Ru ;
Dong, Xiaowu ;
He, Qiaojun ;
Yang, Bo ;
Hu, Yongzhou .
ARCHIV DER PHARMAZIE, 2009, 342 (03) :165-172