Syntheses of bis(3′-indolyl)-2(1H)-pyrazinones

被引:32
作者
Jiang, B [1 ]
Gu, XH [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
bisinoble alkaloid; dipeptidyl aldehyde; bisindolyl ketone amine; cyclization;
D O I
10.3987/COM-00-8887
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of 3,6-bis(3'-indolyl)-2(1H)-pyrazinone and 3,5-bis(3'-indolyl)-2( 1H)-pyrazinone were described. Syntheses of 3,6-bis(3 '-indolyl)2(1H)-pyrazinone proceeded through the condensation of N-Boc-indolylglycine with indol-3-yl-N-methyl-O-methoxyglycinamide, and followed by reduction with LiAlH4 and cyclization of the resulting bisindolyl aldehyde-amine. 3,5-Bis(3'-indolyl)-2(1H)-pyrazinone was synthesized by cyclization of bisindolyl ketone amine in excess of ammonia under pressure.
引用
收藏
页码:1559 / 1568
页数:10
相关论文
共 23 条
[1]   SYNTHESIS AND REACTIONS OF SOME 3-(2-HALOACYL)INDOLES [J].
BERGMAN, J ;
BACKVALL, JE ;
LINDSTRO.JO .
TETRAHEDRON, 1973, 29 (07) :971-976
[2]  
BRADBURY RH, 1990, HETEROCYCLES, V31, P1647
[3]   NOVEL THIAZOLE DERIVATIVES AS INHIBITORS OF SUPEROXIDE PRODUCTION BY HUMAN NEUTROPHILS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
CHIHIRO, M ;
NAGAMOTO, H ;
TAKEMURA, I ;
KITANO, K ;
KOMATSU, H ;
SEKIGUCHI, K ;
TABUSA, F ;
MORI, T ;
TOMINAGA, M ;
YABUUCHI, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (02) :353-358
[4]   Syntheses of 7-carboxyindolylglycines utilising glycine cation equivalents [J].
Clark, BP ;
Harris, JR .
SYNTHETIC COMMUNICATIONS, 1997, 27 (24) :4223-4234
[5]  
COREY EJ, 1975, TETRAHEDRON LETT, P3117
[6]   BROP - A NEW REAGENT FOR COUPLING N-METHYLATED AMINO-ACIDS [J].
COSTE, J ;
DUFOUR, MN ;
PANTALONI, A ;
CASTRO, B .
TETRAHEDRON LETTERS, 1990, 31 (05) :669-672
[7]  
Faulkner DJ, 1999, NAT PROD REP, V16, P155
[8]  
FEHRENTZ JA, 1982, SYNTHESIS-STUTTGART, P676
[9]   RAPID REMOVAL OF PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH 1,4-CYCLOHEXADIENE [J].
FELIX, AM ;
HEIMER, EP ;
LAMBROS, TJ ;
TZOUGRAKI, C ;
MEIENHOFER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4194-4196
[10]   Syntheses and biological activities of bis(3-indolyl)thiazoles, analogues of marine bis(indole)alkaloid nortopsentins [J].
Gu, XH ;
Wan, XZ ;
Jiang, B .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (04) :569-572