Inverse electron demand Diels-Alder reactions of indole .5. Reactions of 3-substituted indoles with heteroaromatic azadienes.

被引：24

作者：

Benson, SC ^{[1
]}

Lee, L ^{[1
]}

Snyder, JK ^{[1
]}

机构：

[1] BOSTON UNIV,DEPT CHEM,BOSTON,MA 02215

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 29期

关键词：

D O I：

10.1016/0040-4039(96)01017-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The inverse electron demand Diels-Alder reactions of 3-substituted indoles with 1,2,4-triazines and 1,2,4,5-tetrazines proceeded in excellent yields both inter- and intramolecularly. The cycloaddition of tryptophan with a tethered 1,2,4-triazine produced a diastereomerically pure cycloadduct. Copyright (C) 1996 Elsevier Science Ltd

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页码：5061 / 5064

页数：4

相关论文

共 37 条

[1] FACILE CYCLO-ADDITION OF 2-PHENYLSULFONYL 1,3-DIENES TO INDOLES [J].

BACKVALL, JE ;

PLOBECK, NA ;

JUNTUNEN, SK .

TETRAHEDRON LETTERS, 1989, 30 (19) :2589-2592

[2]

BAKKEGARD K, UINPUB

[3] PREPARATION OF N,O-AMINALS AS SYNTHETIC EQUIVALENTS OF H2C=NAR AND (H2C=NHAR)+ IONS - NEUTRAL-PROMOTED AND ACID-PROMOTED TRANSFORMATIONS [J].

BARLUENGA, J ;

BAYON, AM ;

CAMPOS, P ;

ASENSIO, G ;

GONZALEZNUNEZ, E ;

MOLINA, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1631-1636

[4] INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS .3. INTRAMOLECULAR REACTIONS WITH 1,2,4-TRIAZINES TO ACCESS THE CANTHINE SKELETON [J].

BENSON, SC ;

LI, JH ;

SNYDER, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5285-5287

[5] INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - 5H-PYRIDAZINO[4,5-B]INDOLES AS CYCLOADDUCTS WITH 3,6-DICARBOMETHOXY-1,2,4,5-TETRAZINE [J].

BENSON, SC ;

PALABRICA, CA ;

SNYDER, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4610-4614

[6] INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - REACTIONS WITH 1,2,4-TRIAZINES AND 1,2-DIAZINES [J].

BENSON, SC ;

GROSS, JL ;

SNYDER, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3257-3269

[7]

BENSON SC, INDOLE DIENOPHILE IN

[8]

Boger D.L., 1987, ORGANIC CHEM MONOGRA, V47

[9] A DETAILED, CONVENIENT PREPARATION OF DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE [J].

BOGER, DL ;

COLEMAN, RS ;

PANEK, JS ;

HUBER, FX ;

SAUER, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5377-5379

[10] DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - TOTAL SYNTHESIS OF PDE-II METHYL-ESTER [J].

BOGER, DL ;

COLEMAN, RS .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3250-3252

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