Zn‐Mediated Synthesis Of 3‐Substituted Indoles Using A Three‐Component Reaction Approach
D. Anselmo, Eduardo C. Escudero-Adán, M. Belmonte, A. Kleij
Published 2012 · Chemistry
Twitter
Facebook
LinkedIn
Email The synthesis of 3-substituted indoles was investigated through a multicomponent reaction (MCR) approach by using aldehydes, indole and malononitrile as the reagents. The reaction was catalyzed by Lewis acidic Zn(salphen) complexes and their performance was compared with a number of other ZnII structures and M(salphen)s, which showed the Zn(salphen)s to be superior. However, the complex nature of this three-component reaction (3-CR) results in substantial byproduct formation that arises from the intermediate benzylidene malononitrile species. The 3-CR was studied in detail that covered the influence of the base, solvent, reagent stoichiometry and also involved stability studies. The results led to a mechanistic proposal in which the benzylidene malononitrile intermediate plays a central role; it is one of the major species that is formed in most of the catalytic reactions studied. Furthermore, it provided a prelude for the in situ reaction with the malononitrile reagent, which most probably affords a complex mixture of N-containing heterocycles.
This paper references
10.1039/B608164A
Chemo-differentiating ABB' multicomponent reactions. Privileged building blocks.
D. Tejedor (2007)
10.1039/b902866h
Zinc-centred salen complexes: versatile and accessible supramolecular building motifs.
A. Kleij (2009)
10.1021/JA036191Y
The total synthesis of (+)-hapalindole Q by an organomediated Diels-Alder reaction.
A. C. Kinsman (2003)
10.1039/B316241A
Simple indole alkaloids and those with a nonrearranged monoterpenoid unit
M. Somei (2001)
10.1021/AR000048H
Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog.
C. O. Kappe (2000)
10.1021/IC701245R
Expedient method for the transmetalation of Zn(II)-centered salphen complexes.
Eduardo C Escudero-Adán (2007)
10.1002/ADSC.200800239
Chiral Brønsted Acid‐Mediated Enantioselective Organocatalytic Three‐Component Reaction for the Construction of Trifluoromethyl‐Containing Molecules
Guang-Wu Zhang (2008)
10.1039/c0cc05695b
Synthesis of 3-indole derivatives by copper sulfonato Salen catalyzed three-component reactions in water.
Yanyang Qu (2011)
10.1002/EJIC.201000487
From Salicylaldehyde to Chiral Salen Sulfonates – Syntheses, Structures and Properties of New Transition Metal Complexes Derived from Sulfonato Salen Ligands
E. Delahaye (2010)
10.1021/ja711349r
Enzyme-like chemoselective acylation of alcohols in the presence of amines catalyzed by a tetranuclear zinc cluster.
T. Ohshima (2008)
10.1002/ANGE.200903803
Asymmetric Organocatalytic Cascade Reactions with α‐Substituted α,β‐Unsaturated Aldehydes
Patrizia Galzerano (2009)
10.1021/i300010a042
"Chemical Mixed" catalysts
I. Pearson (1983)
10.1021/CR0505728
Recent developments in isocyanide based multicomponent reactions in applied chemistry.
A. Dömling (2006)
10.1002/chem.200801149
New templating strategies with salen scaffolds (Salen=N,N'-bis(salicylidene)ethylenediamine dianion).
A. Kleij (2008)
10.1016/J.CATCOM.2008.01.002
Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions
Caibo Yue (2008)
10.1002/1521-3757(20000915)112:18<3300::AID-ANGE3300>3.0.CO;2-Z
Multikomponentenreaktionen mit Isocyaniden
A. Dömling (2000)
10.1002/JHET.5570370322
Since 1995 the new chemistry of multicomponent reactions and their libraries, including their heterocyclic chemistry
I. Ugi (2000)
10.1039/B605066B
Direct conversion of esters, lactones, and carboxylic acids to oxazolines catalyzed by a tetranuclear zinc cluster.
T. Ohshima (2006)
10.1002/chem.200900146
Trapping of a four-coordinate zinc salphen complex inside a crystal matrix.
Eduardo C Escudero-Adán (2009)
10.1021/OL062031Q
Carboxylic acid catalyzed three-component aza-Friedel-Crafts reactions in water for the synthesis of 3-substituted indoles.
S. Shirakawa (2006)
10.1039/C0NJ00691B
Synthesis of 5-arylidene-2,4-thiazolidinediones by Knoevenagel condensation catalyzed by baker's yeast
Umesh Pratap (2011)
10.1002/cctc.201100031
Ambient Fixation of Carbon Dioxide using a ZnIIsalphen Catalyst
A. Decortes (2011)
10.1016/S0040-4039(99)01349-0
The gramine route to the Diels-Alder adducts of indolo-2,3-quinodimethanes
Khalid Diker (1999)
10.1002/anie.201004957
Effective chirogenesis in a bis(metallosalphen) complex through host-guest binding with carboxylic acids.
S. Wezenberg (2011)
10.1039/c000493f
Efficient carbonate synthesis under mild conditions through cycloaddition of carbon dioxide to oxiranes using a Zn(salphen) catalyst.
A. Decortes (2010)
10.1002/CHEM.200500227
Zn(II)-salphen complexes as versatile building blocks for the construction of supramolecular box assemblies.
A. Kleij (2005)
10.1016/J.BMCL.2004.01.071
1,2,3,4-tetrahydrocarbazoles as 5-HT6 serotonin receptor ligands.
Jean Chang-Fong (2004)
10.1021/i300010a041
Improved synthesis of basic zinc acetate, hexakis(.mu.-acetato)-.mu.-oxotetrazinc
A. C. Poshkus (1983)
10.1039/B700723J
Zinc–salophen complexes as selective receptors for tertiary amines
A. D. Cort (2007)
This paper is referenced by
10.1016/J.TET.2015.10.027
l-Proline-catalyzed multicomponent synthesis of 3-indole derivatives
Yan-Hong He (2015)
10.1002/9783527675944.CH4
Zinc‐Catalyzed Friedel–Crafts Reactions
Yonghai Hui (2015)
10.1080/00397911.2017.1394467
Cu(I)-phosphine complex: An efficient catalyst for synthesis of 3-indole derivatives through one-pot MCR under mild conditions
Avvari N. Prasad (2018)
10.1002/SLCT.201802702
Ultrasonication‐Assisted Synthesis of 3‐Substituted Indoles in Water Using Polymer Grafted ZnO Nanoparticles as Eco‐Friendly Catalyst
Tauhid Shaikh (2019)
10.1002/ADSC.201300162
An Efficient Tetrabutylammonium Fluoride (TBAF)‐Catalyzed Three‐Component Synthesis of 3‐Substituted Indole Derivatives under Solvent‐Free Conditions
Neetu Singh (2013)
10.1016/J.TETLET.2015.02.058
[TBA][Gly] ionic liquid promoted multi-component synthesis of 3-substituted indoles and indolyl-4H-chromenes
U. Chinna Rajesh (2015)
10.1039/C7NJ00249A
Morphology controlled phosphate grafted SnO2–ZrO2 nanocomposite oxides prepared by a urea hydrolysis method as efficient heterogeneous catalysts towards the synthesis of 3-substituted indoles
Sagnika Pradhan (2017)
10.1021/SC500594W
RGO/ZnO Nanocomposite: An Efficient, Sustainable, Heterogeneous, Amphiphilic Catalyst for Synthesis of 3-Substituted Indoles in Water
U. C. Rajesh (2015)
10.1039/C2GC35635J
Multicomponent reactions in unconventional solvents: state of the art
Y. Gu (2012)
10.1002/slct.201904146
Zinc‐Catalysed Multi‐Component Reactions: An Overview
Mohan Neetha (2020)
10.1016/J.CRCI.2016.09.004
Facile synthesis of 3-substituted indoles containing highly polarized double bonds
Mehdi Omidi (2016)
10.3390/CATAL9050409
H3PW12O40/SBA-15 for the Solventless Synthesis of 3-Substituted Indoles
Reza Tayebee (2019)
10.1016/J.TETLET.2017.09.003
Electrochemical approach for synthesis of 3-substituted indole derivatives
Vinay Kr Singh (2017)
10.1070/RCR4780
Salicylaldehydes, as the Privileged Synthons in Multicomponent Reactions
Majid Momahed Heravi (2018)
10.1016/J.TET.2017.08.030
H5PW10V2O40@VOx/SBA-15-NH2 catalyst for the solventless synthesis of 3-substituted indoles
Narges Mahdizadeh Ghohe (2017)
10.3184/174751916X14622783380474
Efficient Synthesis of 3-Substituted Indoles via a Base-Free Copper-Catalysed Three-Component Reaction in Water
Haojie Jiang (2016)
10.1039/C7RA13321A
Recent advances in the application of indoles in multicomponent reactions
Ghodsi Mohammadi Ziarani (2018)
10.1039/C5NJ01288K
Facile construction of 3-indolochromenes and 3-indoloxanthenes via EDDF catalyzed one-pot three component reactions
A. Thakur (2015)
Some data provided by SemanticScholar