Novel synthesis of fused indoles and 2-substituted indoles by the palladium-catalyzed cyclization of N-cycloalkenyl-o-haloanilines

被引：25

作者：

Maruyama, Jun ^{[1
]}

Yamashita, Hiromichi ^{[1
]}

Watanabe, Takeshi ^{[1
]}

Arai, Shigeru ^{[1
]}

Nishida, Atsushi ^{[1
]}

机构：

[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 07期

关键词：

Indole; Palladium; Heck reaction; Olefin isomerization; Enamine; INTRAMOLECULAR HECK REACTION; ONE-POT SYNTHESIS; ASYMMETRIC-SYNTHESIS; ANNULATION; ENAMINONES; NITROGEN; DECALIN; WITTIG;

D O I：

10.1016/j.tet.2008.12.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A now palladium-catalyzed cyclization of N-alkenyl-o-haloanilines with selective isomerization of a double bond followed by formal 5-endo-trig cyclization was developed. A variety of fused and 2-substituted indoles were synthesized from enaminoesters; prepared by condensation of beta-ketoesters and o-iodoaniline. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1327 / 1335

页数：9

共 44 条

[1] Hydroamination/Heck reaction sequence for a highly regioselective one-pot synthesis of indoles using 2-chloroaniline [J].

Ackermann, L ;

Kaspar, LT ;

Gschrei, CJ .

CHEMICAL COMMUNICATIONS, 2004, (24) :2824-2825

[2] ALKALOIDS OF KOPSIA-LAPIDILECTA [J].

AWANG, K ;

SEVENET, T ;

PAIS, M ;

HADI, AHA .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07) :1134-1139

[3] Enantioselective total synthesis of avrainvillamide and the stephacidins [J].

Baran, Phil S. ;

Hafensteiner, Benjamin D. ;

Ambhaikar, Narendra B. ;

Guerrero, Carlos A. ;

Gallagher, John D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8678-8693

[4] Cascade alkenyl amination/heck reaction promoted by a bifunctional palladium catalyst:: A novel one-pot synthesis of indoles from o-haloanilines and alkenyl halides [J].

Barluenga, J ;

Fernández, MA ;

Aznar, F ;

Valdés, C .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2276-2283

[5] Compared reactivity of heterocyclic enaminones: Photochemical and palladium catalyzed synthesis of 6,7,8,9-tetrahydro-5H-pyrido[3,2-b]ind-9-ones [J].

Blache, Y ;

SinibaldiTroin, ME ;

Voldoire, A ;

Chavignon, O ;

Gramain, JC ;

Teulade, JC ;

Chapat, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8553-8556

[6] Intramolecular Heck couplings and cycloisomerizations of bromodienes and enynes with 1′,1′-disubstituted methylenecyclopropane terminators:: Efficient syntheses of [3]dendralenes [J].

Bräse, S ;

Wertal, H ;

Frank, D ;

Vidovic, D ;

de Meijere, A .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (19) :4167-4178

[7] Observations on the intramolecular Heck reactions of aromatic chlorides using palladium/imidazolium salts [J].

Caddick, S ;

Kofie, W .

TETRAHEDRON LETTERS, 2002, 43 (51) :9347-9350

[8] Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones [J].

Chen, CY ;

Lieberman, DR ;

Larsen, RD ;

Verhoeven, TR ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2676-2677

[9]

CHEN LC, 1994, SYNLETT, P759

[10] PALLADIUM-MEDIATED 6-ENDO-TRIG INTRAMOLECULAR CYCLIZATION OF N-ACRYLOYL-7-BROMOINDOLINES - A REGIOCHEMICAL VARIANT OF THE INTRAMOLECULAR HECK REACTION [J].

DANKWARDT, JW ;

FLIPPIN, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2312-2313

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