Bronsted acidic ionic liquid-catalyzed tandem trimerization of indoles: An efficient approach towards the synthesis of indole 3,3′-trimers under solvent-free conditions

被引：15

作者：

Chatterjee, Rana ^{[1
]}

Santra, Sougata ^{[2
]}

Zyryanov, Grigory V. ^{[2
,3
]}

Majee, Adinath ^{[1
]}

机构：

[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India

[2] Ural Fed Univ, Chem Engn Inst, Dept Organ & BioMol Chem, Ekaterinburg, Russia

[3] Russian Acad Sciences, I Ya Postovsky Inst Organ Synth, Ural Div, Ekaterinburg, Russia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2020年 / 57卷 / 04期

基金：

俄罗斯科学基金会;

关键词：

ROOM-TEMPERATURE; MOLTEN-SALT; BIS(INDOLYL)METHANE DERIVATIVES; REGIOSELECTIVE SYNTHESIS; VIBRIO-PARAHAEMOLYTICUS; GLYCINE DERIVATIVES; MEDIATED SYNTHESIS; ACTIVATION; ORGANOCATALYST; ALKYLATION;

D O I：

10.1002/jhet.3914

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have observed the role of 1-butane sulfonic acid-3-methylimidazolium tosylate, [BSMIM]OTs, as an organocatalyst for the tandem type trimerization of indoles to synthesize indole 3,3 '-trimers under neat conditions. Using this developed protocol synthesis of indole trimers with various substituted indoles, which are biologically important, has been reported. From the control experiments and literature, a possible mechanism has been proposed via the generation of indolinium cation in the presence of the ionic liquid catalyst. The catalyst has been recycled for several times. The significant advantages of our methodology are clean reaction with very short time, no chromatography for purification, commercially available substrates, neat reaction conditions, and in the absence of metal. Using the protocol, the MDM2-p53 inhibitor has been synthesized in gram scale with high yield.

引用

页码：1863 / 1874

页数：12

共 106 条

[61] Bronsted acidic ionic liquid-catalyzed tandem reaction: an efficient approach towards regioselective synthesis of pyrano[3,2-c]coumarins under solvent-free conditions bearing lower E-factors [J].

Mahato, Sachinta ;

Santra, Sougata ;

Chatterjee, Rana ;

Zyryanov, Grigory V. ;

Hajra, Alakananda ;

Majee, Adinath .

GREEN CHEMISTRY, 2017, 19 (14) :3282-3295

[62] Bis(indolyl)methane derivatives as highly selective colourimetric and ratiometric fluorescent molecular chemosensors for Cu2+ cations [J].

Martinez, Rosario ;

Espinosa, Arturo ;

Tarraga, Alberto ;

Molina, Pedro .

TETRAHEDRON, 2008, 64 (09) :2184-2191

[63] Efficient, rapid synthesis of bis(indolyl)methane using ethyl ammonium nitrate as an ionic liquid [J].

Mulla, Shafeek A. R. ;

Sudalai, A. ;

Pathan, Mohsinkhan Y. ;

Siddique, Shafi A. ;

Inamdar, Suleman M. ;

Chavan, Santosh S. ;

Reddy, R. Santosh .

RSC ADVANCES, 2012, 2 (08) :3525-3529

[64] A new generation of aprotic yet Bronsted acidic imidazolium salts: low toxicity, high recyclability and greatly improved activity [J].

Myles, Lauren ;

Gore, Rohitkumar G. ;

Gathergood, Nicholas ;

Connon, Stephen J. .

GREEN CHEMISTRY, 2013, 15 (10) :2740-2746

[65] The catalytic versatility of low toxicity dialkyltriazolium salts: in situ modification facilitates diametrically opposed catalysis modes in one pot [J].

Myles, Lauren ;

Gathergood, Nicholas ;

Connon, Stephen J. .

CHEMICAL COMMUNICATIONS, 2013, 49 (46) :5316-5318

[66] Highly recyclable, imidazolium derived ionic liquids of low antimicrobial and antifungal toxicity: A new strategy for acid catalysis [J].

Myles, Lauren ;

Gore, Rohitkumar ;

Spulak, Marcel ;

Gathergood, Nicholas ;

Connon, Stephen J. .

GREEN CHEMISTRY, 2010, 12 (07) :1157-1162

[67] Marine Bacteria, XLVII - Psychrotolerant Bacteria from Extreme Antarctic Habitats as Producers of Rare Bis- and Trisindole Alkaloids [J].

Nair, Vimal ;

Schuhmann, Imelda ;

Anke, Heidrun ;

Kelter, Gerhard ;

Fiebig, Heinz-Herbert ;

Helmke, Elisabeth ;

Laatsch, Hartmut .

PLANTA MEDICA, 2016, 82 (9-10) :910-918

[68] Synthesis, characterization and photophysical properties of some 3,3′-bisindolyl(aryl)methanes [J].

Neshat, Abdollah .

RSC ADVANCES, 2016, 6 (39) :32839-32848

[69] STRUCTURE ELUCIDATION OF STREPTINDOLE, A NOVEL GENOTOXIC METABOLITE ISOLATED FROM INTESTINAL BACTERIA [J].

OSAWA, T ;

NAMIKI, M .

TETRAHEDRON LETTERS, 1983, 24 (43) :4719-4722

[70]

Pal B., 2005, CATAL COMMUN, V6, P711, DOI DOI 10.1016/J.CATCOM.2005.07.003

← 2 3 4 5 6 7 8 9 10 11 →