A mild and environmentally friendly scandium(III) trifluoromethanesulfonate-catalyzed synthesis of bis(3′-indolyl) alkanes and bis(3′-indolyl)-1-deoxyalditols

被引：38

作者：

Sato, S ^{[1
]}

Sato, T ^{[1
]}

机构：

[1] Yamagata Univ, Fac Engn, Yonezawa, Yamagata 9928510, Japan

来源：

CARBOHYDRATE RESEARCH | 2005年 / 340卷 / 14期

关键词：

bis(3 '-indolyl)alkanes; 1-deoxyalditol; acyclic C-nucleoside; Sc(OTf)(3); aqueous media;

D O I：

10.1016/j.carres.2005.07.019

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Bis(3'-indolyl)alkanes and bis(3'-indolyl) derivatives containing a 1-deoxyalditol moiety were synthesized in the presence of 5 mol % of scandium(III) trifluoromethanesulfonate [Sc(OTf)(3)] in CH3CN or EtOH-H2O mixture as a solvent from room temperature to 70 degrees C in good yields (78-97%). (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2251 / 2255

页数：5

共 25 条

[1]

Chakrabarty M, 2001, HETEROCYCLES, V55, P2431

[2] The reactions of nitrones with indoles [J].

Chalaye-Mauger, H ;

Denis, JN ;

Averbuch-Pouchot, MT ;

Vallée, Y .

TETRAHEDRON, 2000, 56 (05) :791-804

[3] Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones [J].

Chen, DP ;

Yu, LB ;

Wang, PG .

TETRAHEDRON LETTERS, 1996, 37 (26) :4467-4470

[4] Acyclic C-nucleosides: synthesis of chiral 1,1-diheteroaryl-alditols and X-ray crystal structure of 2,3,5-tri-O-benzyl-1,1-di-(2'-pyrryl)-1-deoxy-D-arabinitol [J].

Cornia, M ;

Capacchi, S ;

DelPogetto, M ;

Pelosi, G ;

Fava, GG .

TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2905-2912

[5] The reaction of nitrones with indoles. Synthesis of asymmetrical diindolylalcanes [J].

Denis, JN ;

Mauger, H ;

Vallee, Y .

TETRAHEDRON LETTERS, 1997, 38 (49) :8515-8518

[6]

GUERRI FA, 1981, CHEM LETT, P511

[7]

HOGAN IT, 1984, SYNTHESIS-STUTTGART, P872

[8] Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions [J].

Ji, SJ ;

Wang, SY ;

Zhang, Y ;

Loh, TP .

TETRAHEDRON, 2004, 60 (09) :2051-2055

[9]

JULIA M, 1965, B SOC CHIM FR, P2175

[10] SYNTHESES OF SOME SUBSTITUTED DI-INDOLYL-METHANES IN AQUEOUS MEDIUM AT ROOM TEMPERATURE [J].

KAMAL, A ;

QURESHI, AA .

TETRAHEDRON, 1963, 19 (04) :513-&

← 1 2 3 →