Synthesis of indoles upon sequential reaction of 3-alkynylpyrrole-2-carboxaldehydes with iodonium ions and alkenes.: Preparation of related benzofuran and benzothiophene derivatives

被引：55

作者：

Barluenga, J ^{[1
]}

Vázquez-Villa, H ^{[1
]}

Ballesteros, A ^{[1
]}

González, JM ^{[1
]}

机构：

[1] Univ Oviedo, CSIC, Unidad Asociada, Inst Univ Quim Organometal Enrique Moles, E-33006 Oviedo, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2005年 / 347卷 / 04期

关键词：

alkenes; enamines; indoles; iodine; pyrroles;

D O I：

10.1002/adsc.200404293

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Di- and trisusbstituted indoles 2 have been prepared by reaction of pyrroles 1 with alkenes via iodonium-induced benzannulation reaction. Enamines and enol ethers are also useful partners in that cyclisation process. This regioselective transformation can be easily adapted to prepare related benzofuran and benzothiophene skeletons.

引用

页码：526 / 530

页数：5

共 55 条

[1] A simple, two-step synthesis of 3-iodoindoles [J].

Amjad, M ;

Knight, DW .

TETRAHEDRON LETTERS, 2004, 45 (03) :539-541

[2]

[Anonymous], INDOLES

[3] Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines [J].

Aoyagi, Y ;

Mizusaki, T ;

Ohta, A .

TETRAHEDRON LETTERS, 1996, 37 (51) :9203-9206

[4] Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles [J].

Arcadi, A ;

Bianchi, G ;

Marinelli, F .

SYNTHESIS-STUTTGART, 2004, (04) :610-618

[5] AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].

Asao, N ;

Aikawa, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459

[6] Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].

Asao, N ;

Kasahara, T ;

Yamamoto, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506

[7] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].

Asao, N ;

Nogami, T ;

Lee, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925

[8] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[9]

Asao T., 2003, ANGEW CHEM, V115, P3628

[10] Intramolecular arylation reactions of alkenes:: A flexible approach to chromans and tetrahydroquinoline derivatives [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3416-3417

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