Redox-Neutral Indole Annulation Cascades

被引：178

作者：

Haibach, Michael C. ^{[1
]}

Deb, Indubhusan ^{[1
]}

De, Chandra Kanta ^{[1
]}

Seidel, Daniel ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 07期

基金：

美国国家科学基金会;

关键词：

C-H BOND; RING-CLOSURE REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; ONE-POT SYNTHESIS; INTERMOLECULAR REACTIONS; CYCLOADDITION REACTION; CATALYZED CYCLIZATION; 1,5-HYDRIDE SHIFTS; ORGANIC-SYNTHESIS; ALKYNYL ETHERS;

D O I：

10.1021/ja110713k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-catalyzed redox-neutral annulation proceeds via a condensation/1,5-hydride shift/ring-closure sequence. Polycyclic azepinoindoles and related compounds are obtained in a single step with good to excellent yields.

引用

页码：2100 / 2103

页数：4

共 99 条

[1] Domino reactions initiated by intramolecular hydride transfers from tri(di)arylmethane fragments to ketenimine and carbodiimide functions [J].

Alajarin, Mateo ;

Bonillo, Baltasar ;

Ortin, Maria-Mar ;

Sanchez-Andrada, Pilar ;

Vidal, Angel ;

Orenes, Raul-Angel .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4690-4700

[2] Unexpected Formation of 2,1-Benzisothiazol-3-ones from Oxathiolano Ketenimines: A Rare Tandem Process [J].

Alajarin, Mateo ;

Bonillo, Baltasar ;

Sanchez-Andrada, Pilar ;

Vidal, Angel ;

Bautista, Delia .

ORGANIC LETTERS, 2009, 11 (06) :1365-1368

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4] Gold(I)-catalyzed intermolecular addition of carbon nucleophiles to 1,5- and 1,6-enynes [J].

Amijs, Catelijne H. M. ;

Lopez-Carrillo, Veronica ;

Raducan, Mihai ;

Perez-Galan, Patricia ;

Ferrer, Catalina ;

Echavarren, Antonio M. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7721-7730

[5] Gold-catalyzed conjugate addition type reaction of indoles with α,β-enones [J].

Arcadi, A ;

Bianchi, G ;

Chiarini, M ;

D'anniballe, G ;

Marinelli, F .

SYNLETT, 2004, (06) :944-950

[6] 1,5-HYDRIDE SHIFTS IN ACYCLIC SYSTEMS CONTAINING ALPHA BETA-UNSATURATED KETONES AND PARA-METHOXYPHENYL GROUPS [J].

ATKINSON, RS ;

GREEN, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (03) :394-401

[7]

ATKINSON RS, 1969, CHEM COMMUN, P735

[8] C-2/C-3 annulation and C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters [J].

Bajtos, Barbora ;

Yu, Ming ;

Zhao, Hongda ;

Pagenkopf, Brian L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) :9631-9634

[9] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[10] [1,5]-hydride transfer/cyclizations on alkynyl Fischer carbene complexes:: Synthesis of 1,2-dihydroquinolinyl carbene complexes and cascade reactions [J].

Barluenga, Jose ;

Fananas-Mastral, Martin ;

Aznar, Fernando ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6594-6597

← 1 2 3 4 5 6 7 8 9 10 →