Recent advances in the application of indoles in multicomponent reactions

Ziarani, Ghodsi Mohammadi; Moradi, Razieh; Lashgari, Negar

doi:10.1039/c7ra13321a

Cited by 99 publications

(44 citation statements)

References 156 publications

(148 reference statements)

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“…To further explore the potential of microwave-assisted carbocatalysis, the Fischer indole synthesis, a reaction commonly employed to prepare biologically active heterocycles, was selected 36 . As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Asphaltene oxide promotes a broad range of synthetic transformations

Jung

Bielawski

2019

Commun Chem

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Carbocatalysts, which are catalytically-active materials derived from carbon-rich sources, are attractive alternatives to metal-based analogs. Graphene oxide is a prototypical example and has been successfully employed in a broad range of synthetic transformations. However, its use is accompanied by a number of practical and fundamental drawbacks. For example, graphene oxide undergoes explosive decomposition when subjected to elevated temperatures or microwaves. We found that asphaltene oxide, an oxidized collection of polycyclic aromatic hydrocarbons that are often discarded from petroleum refining processes, effectively overcomes the drawbacks of using graphene oxide in synthetic chemistry and constitutes a new class of carbocatalysts. Here we show that asphaltene oxide may be used to promote a broad range of transformations, including Claisen-Schmidt condensations, CC cross-couplings, and Fischer indole syntheses, as well as chemical reactions which benefit from the use of microwave reactors.

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Section: Resultsmentioning

confidence: 99%

Asphaltene oxide promotes a broad range of synthetic transformations

Jung

Bielawski

2019

Commun Chem

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“…Indole is a pervasive and naturally occurring heterocyclic compound, the structure of which comprises of a six-membered benzene ring tethered to a five-membered pyrrole ring [5] (Figure 1). With its 10 π-electrons, indole follows Huckel's rule of aromaticity.…”

Section: Indole and Its Pharmacological Significancementioning

confidence: 99%

Role of Indole Scaffolds as Pharmacophores in the Development of Anti-Lung Cancer Agents

Dhuguru

Skouta

2020

Molecules

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Lung cancer is the leading cause of death in men and women worldwide, affecting millions of people. Between the two types of lung cancers, non-small cell lung cancer (NSCLC) is more common than small cell lung cancer (SCLC). Besides surgery and radiotherapy, chemotherapy is the most important method of treatment for lung cancer. Indole scaffold is considered one of the most privileged scaffolds in heterocyclic chemistry. Indole may serve as an effective probe for the development of new drug candidates against challenging diseases, including lung cancer. In this review, we will focus on discussing the existing indole based pharmacophores in the clinical and pre-clinical stages of development against lung cancer, along with the synthesis of some of the selected anti-lung cancer drugs. Moreover, the basic mechanism of action underlying indole based anti-lung cancer treatment, such as protein kinase inhibition, histone deacetylase inhibition, DNA topoisomerase inhibition, and tubulin inhibition will also be discussed.

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“…As mentioned above, the increasing interest on indole-chemistry and also on Pd(II)-allyl complexes is mainly due to their potential utility in synthesis and catalysis [1][2][3][4][5][25][26][27][28]34,35,[42][43][44]. However, as far as we know, the use of 2-phenyl-3H-indoles or their transition metal complexes in homogeneous catalysis still remains unexplored.…”

Section: Allylic Alkylation Reactionsmentioning

confidence: 99%

“…Indole is one of the most important heterocycles for its presence in bioactive natural products, pharmaceuticals, and agrochemicals [1][2][3][4][5][6][7][8][9]. Indole derivatives are not only "privileged structures" in Medicinal Chemistry [1][2][3][4]6,[10][11][12], due to their biological activity, but also valuable reagents for the design and synthesis of compounds with interesting properties and applications in a variety of fields [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. The construction and functionalization of indoles have been studied since long ago; however, and as mentioned by Prof. M. Bandini some years ago "this field had a formidable boom across the new millennium when catalysis started revolutionizing the chemistry of indole" [7].…”

Section: Introductionmentioning

confidence: 99%

“…The construction and functionalization of indoles have been studied since long ago; however, and as mentioned by Prof. M. Bandini some years ago "this field had a formidable boom across the new millennium when catalysis started revolutionizing the chemistry of indole" [7]. Interesting applications of novel indole derivatives as dyes [1][2][3]13], as components of Dye Sensitized Solar Cells (DSSC) [1][2][3]5] and as precursors in synthesis of organic compounds, including some natural products, have been reported [1][2][3]15,17].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, Solution Behavior and Theoretical Studies of Pd(II) Allyl Complexes with 2-Phenyl-3H-indoles as Ligands

et al. 2019

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The study of the reactivity of three 2-phenyl-3H-indole ligands of general formulae C8H3N-2-(C6H4-4-R1)-3-NOMe-5-R2 (1) [with R1 = H, R2 = OMe (a); R1 = R2 = H (b) or R1 = Cl, R2 = H (c)] with [Pd(η3-1-R3C3H4)(μ-Cl)]2 (R3 = H or Ph) has allowed us to isolate two sets of new Pd(II)-allyl complexes of general formulae [Pd(η3-1-R3C3H4)(1)Cl] {R3 = H (2) or Ph (3)}. Compounds 2a–2c and 3a–3c were characterized by elemental analyses, mass spectrometry and IR spectroscopy. The crystal structures of 2a, 3a and 3b were also determined by X-ray diffraction. 1H-NMR studies reveal the coexistence of two (for 2a–2c) or three (for 3a–3c) isomeric forms in CD2Cl2 solutions at 182 K. Additional studies on the catalytic activity of mixtures containing [Pd(η3-C3H5)(μ-Cl)]2 and the parent ligand (1a–1c) in the allylic alkylation of (E)-3-phenyl-2-propenyl (cinnamyl) acetate with sodium diethyl 2-methylmalonate as well as the stoichiometric reaction between compounds 3a and 3c with the nucleophile reveal that in both cases the formation of the linear trans- derivative is strongly preferred over the branched product. Computational studies at a DFT level on compound 3a allowed us to compare the relative stability of their isomeric forms present in solution and to explain the regioselectivity of the catalytic and stoichiometric processes.

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Recent advances in the application of indoles in multicomponent reactions

Cited by 99 publications

References 156 publications

Asphaltene oxide promotes a broad range of synthetic transformations

Asphaltene oxide promotes a broad range of synthetic transformations

Role of Indole Scaffolds as Pharmacophores in the Development of Anti-Lung Cancer Agents

Synthesis, Characterization, Solution Behavior and Theoretical Studies of Pd(II) Allyl Complexes with 2-Phenyl-3H-indoles as Ligands

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