REACTIONS OF 2-VINYLINDOLES WITH CARBODIENOPHILES - SYNTHETIC AND MECHANISTIC ASPECTS

被引：79

作者：

EITEL, M ^{[1
]}

PINDUR, U ^{[1
]}

机构：

[1] UNIV MAINZ,DEPT CHEM & PHARM,SAARSTR 21,W-6500 MAINZ 1,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 19期

关键词：

D O I：

10.1021/jo00306a014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of selectively functionalized 2-vinylindoles with acyclic and cyclic carbodienophiles proceed with high regio- and/or stereoselectivities to furnish Diels-Alder adducts, Diels-Alder ene products, and Michael adducts. This methodology provides a convenient route to functionalized indoles, carbazoles, and [c]pyrrolo-annelated carbazoles with substitution patterns that are not easily obtained by the usual routes. Some mechanistic aspects of the chemistry of 2-vinylindoles are discussed. © 1990 American Chemical Society.

引用

页码：5368 / 5374

页数：7

共 49 条

[1]

ALLINGER, QCPE395

[2]

ALLINGER, QCPE318

[3] SYNTHESIS AND BIOLOGICAL PROPERTIES OF SOME 6H-PYRIDO[4,3-B]CARBAZOLES [J].

ARCHER, S ;

ROSS, BS ;

PICAMATTOCCIA, L ;

CIOLI, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (07) :1204-1210

[4] FLASH VACUUM PYROLYSIS OF 5-(INDOL-2-YLMETHYLENE)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE AND 5-(INDOL-3-YLMETHYLENE)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE [J].

BENZIES, DWM ;

FRESNEDA, PM ;

JONES, RA ;

MCNAB, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09) :1651-1654

[5]

BHATTACHARYYA P, 1987, PROG CHEM ORG NAT PR, V52, P160

[6]

CCARDELINA JH, 1979, TETRAHEDRON LETT, P4915

[7]

CLARK T, 1985, COMPUTATIONAL CHEM

[8] GROUND-STATES OF MOLECULES .39. MNDO RESULTS FOR MOLECULES CONTAINING HYDROGEN, CARBON, NITROGEN, AND OXYGEN [J].

DEWAR, MJS ;

THIEL, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :4907-4917

[9] GROUND-STATES OF MOLECULES .38. MNDO METHOD - APPROXIMATIONS AND PARAMETERS [J].

DEWAR, MJS ;

THIEL, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :4899-4907

[10] MECHANISM OF THE DIELS-ALDER REACTION - REACTIONS OF BUTADIENE WITH ETHYLENE AND CYANOETHYLENES [J].

DEWAR, MJS ;

OLIVELLA, S ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :5771-5779

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