NEW DIELS-ALDER REACTIONS OF (E/Z)-2'-METHOXY-SUBSTITUTED 3-VINYLINDOLES WITH CARBODIENOPHILES AND HETERODIENOPHILES - REGIOSELECTIVE AND STEREOSELECTIVE ACCESS TO [B] ANNELATED INDOLES AND FUNCTIONALIZED OR [A] ANNELATED CARBAZOLES

被引：57

作者：

PINDUR, U ^{[1
]}

KIM, MH ^{[1
]}

ROGGE, M ^{[1
]}

MASSA, W ^{[1
]}

MOLINIER, M ^{[1
]}

机构：

[1] UNIV MARBURG,DEPT CHEM,W-3550 MARBURG,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 03期

关键词：

D O I：

10.1021/jo00029a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (E/Z)-2'-methoxy-substituted 3-vinylindoles 1a,b react with some carbo- and azodienophiles to furnish new carbazoles and pyridazinoindoles. The conservation of the E and Z stereochemistry of 1 in these Diels-Alder reactions was investigated, and a mechanistic rationalization is given for the stereoselective and regioselective results observed.

引用

收藏

页码：910 / 915

页数：6

相关论文

共 29 条

[1] INDOLE ALKALOIDS IN MEDICINE [J].

BAN, Y ;

MURAKAMI, Y ;

IWASAWA, Y ;

TSUCHIYA, M ;

TAKANO, N .

MEDICINAL RESEARCH REVIEWS, 1988, 8 (02) :231-308

[2] SYNTHESIS OF CARBAZOLE ALKALOIDS [J].

BERGMAN, J ;

PELCMAN, B .

PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1967-1976

[3]

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

[4] INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF N-SULFONYL ALPHA,BETA-UNSATURATED IMINES - A GENERAL-APPROACH TO IMPLEMENTATION OF THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS [J].

BOGER, DL ;

CORBETT, WL ;

CURRAN, TT ;

KASPER, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1713-1729

[5] DIELS-ALDER REACTIONS OF 1-AZA-1,3-BUTADIENES - ROOM-TEMPERATURE, ENDO-SELECTIVE LUMODIENE-CONTROLLED [4+2]-CYCLOADDITION REACTIONS OF N-SULFONYL-4-(ETHOXYCARBONYL)-1-AZA-1,3-BUTADIENES [J].

BOGER, DL ;

CURRAN, TT .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) :5439-5442

[6] 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

[7] 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

[8] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[9]

FLEMING I, 1976, FRONTIER ORBITALS OR

[10]

GAJEWSKI JJ, 1990, ADV MOL MODELLING, V2, P65