Selective endo and exo iodocyclizations in the synthesis of Quinolines and Indoles

被引：119

作者：

Hessian, KO ^{[1
]}

Flynn, BL ^{[1
]}

机构：

[1] Monash Univ, Victorian Coll Pharm, Dept Med Chem, Parkville, Vic 3052, Australia

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 02期

关键词：

D O I：

10.1021/ol052518j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, efficient method for a divergent synthesis of indoles, quinolines, and quinolinones using a highly selective endo/exo iodocyclization procedure is described.

引用

页码：243 / 246

页数：4

共 32 条

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

Amjad, M ;

Knight, DW .

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

[2] A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].

Arcadi, A ;

Cacchi, S ;

Fabrizi, G ;

Marinelli, F ;

Moro, L .

SYNLETT, 1999, (09) :1432-1434

[3] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines [J].

Arcadi, A ;

Cacchi, S ;

Di Giuseppe, S ;

Fabrizi, G ;

Marinelli, F .

ORGANIC LETTERS, 2002, 4 (14) :2409-2412

[4] RULES FOR RING-CLOSURE - RING FORMATION BY CONJUGATE ADDITION OF OXYGEN NUCLEOPHILES [J].

BALDWIN, JE ;

THOMAS, RC ;

KRUSE, LI ;

SILBERMAN, L .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3846-3852

[5] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[6]

BALDWIN JE, 2001, J CHEM SOC CHEM COMM, P736

[7] Synthesis, X-ray crystal structure and tubulin-binding properties of a benzofuran analogue of the potent cytotoxic agent combretastatin A4 [J].

Banwell, MG ;

Flynn, BL ;

Willis, AC ;

Hamel, E .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (08) :767-774

[8] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409

[9] Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids [J].

Bellina, F ;

Biagetti, M ;

Carpita, A ;

Rossi, R .

TETRAHEDRON, 2001, 57 (14) :2857-2870

[10] A brief synthesis of beta-iodofurans [J].

Bew, SP ;

Knight, DW .

CHEMICAL COMMUNICATIONS, 1996, (09) :1007-1008

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