Benzenesulfonic Acid: A Versatile Catalyst for the Synthesis of Bis(indolyl)methanes as Antioxidants

Simha, Pulla Reddy; Mangali, Madhu Sekhar; Gari, Divya Kuppireddy; Padmavathi, V.; Padmaja, A.

doi:10.1002/jhet.2873

Cited by 12 publications

(6 citation statements)

References 21 publications

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“…Since then, various alternative acids have been applied including protic acids, such as silica-bonded S-sulfonic acid [ 13 ], polyvinylsulfonic acid (PVSA) [ 14 ], kaolin-supported H 2 SO 4 [ 15 ], polyvinylpolypyrrolidone-supported triflic acid (PVPP . OTf) [ 16 ], ascorbic acid [ 17 ], phosphoric acid [ 18 ], benzenesulfonic acid [ 19 ], chitosan–SO 3 H (CTSA) [ 20 ], phthalimide- N -sulfonic acid (PISA) [ 21 ] and SiO 2 -KHSO 4 [ 22 ] as well as Lewis acids, such as FeCl 3 [ 23 – 24 ], RuCl 3 ·3H 2 O [ 25 ], AgNO 3 [ 26 ], glycerol and [Fe(III)-(salen)]Cl [ 27 ], Fe(DS) 3 · n H 2 O [ 28 ], Sc(OTf) 3 [ 29 ], B(C 6 F 5 ) 3 or PhSiCl 3 [ 30 ] and Cp 2 TiCl 2 [ 31 ]. However, most of these reactions face some serious drawbacks, such as the requirement of large quantities of the catalyst due to present moisture or formation of adducts with the substrate, long reaction times, lower yields, and production of large amounts of toxic waste during work-up.…”

Section: Reviewmentioning

confidence: 99%

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Kolagkis,

Galathri,

Kokotos

2024

Beilstein J. Org. Chem.

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The synthesis of indoles and their derivatives, more specifically bis(indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti-inflammatory, and even anticancer agents. Traditionally, the synthesis of BIMs has been achieved upon the acidic condensation of an aldehyde with indole, utilizing a variety of protic or Lewis acids. However, due to the increased environmental awareness of our society, the focus has shifted towards the development of greener synthetic technologies, like photocatalysis, organocatalysis, the use of nanocatalysts, microwave irradiation, ball milling, continuous flow, and many more. Thus, in this review, we summarize the medicinal properties of BIMs and the developed BIM synthetic protocols, utilizing the reaction between aldehydes with indoles, while focusing on the more environmentally friendly methods developed over the years.

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Section: Reviewmentioning

confidence: 99%

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Kolagkis,

Galathri,

Kokotos

2024

Beilstein J. Org. Chem.

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“…4-(1H-Indol-3-yl(4-nitrophenyl)methyl)-N,N-dimethylaniline (4a): [1][2][3] [14][15][16][17][20][21][22]25,27,29,30,[37][38][39]42,55,56]…”

Section: Physical and Spectral Data Of Derivativesmentioning

confidence: 99%

“…3,3'-((4-Bromophenyl)methylene)bis(1H-indole) (5b): [14,17,18,[20][21][22]26,28,29,30,42,55] 4,4'-((4-Bromophenyl)methylene)bis(N,N-dimethylaniline) (6b): [23] CAS Number 57752-00-8; 10% yield (0.0410 g) as a blue solid; m.p. 116-118 °C; Rf = 0.62 (20% EtOAc/n-hexane); [14,[16][17][18][19][20][21][22][25][26][27][28][29][30][37][38][39][40]55,56]…”

Section: Accepted Manuscriptmentioning

confidence: 99%

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Brønsted Acidic Ionic Liquid Catalyzed Three-Component Friedel–Crafts Reaction for the Synthesis of Unsymmetrical Triarylmethanes

Rinkam

Senapak

Watchasit

et al. 2022

Synlett

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convenient and practical methodology for the synthesis of unsymmetrical triarylmethanes was demonstrated through a one-pot three-component double Friedel-Craft reaction between various aliphatic aromatic and heteroaromatic aldehydes, N,N-dialkylanilines and indoles using Bronsted acidic ionic liquid as catalyst. This method was successfully performed under metal- and solvent-free conditions at 80oC, affording the corresponding unsymmetrical triarylmethane products in moderate to high yields with a broad range of substrates. In addition, the mechanistic proposal of this methodology was studied by using quantitative NMR analysis (qNMR).

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“…The 3-substituted indoles are structural units of many natural and biologically interesting compounds, which possess various pharmaco-logically activities. The indole-based derivatives have been investigated for anticancer activities 49 . The reaction of indole with the 4-Nitrobenzaldehyde compound in the presence of 5-mol% benzene-sulfonic acid in acetonitrile solvent performed to synthesize 3,3''-((4-Nitrophenyl) methylene) bis (1H-indole) compound is observed that the reaction proceeded in shorter reaction times and times and in high yield in the ultrasonic method than compare to the conventional method.…”

Section: Fig 19: One-pot Three Component Coupling Reaction Scheme Ofmentioning

confidence: 99%

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2019

IJPSR

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Indole and coumarin are the most versatile and cogent heterocyclic scaffolds which are not only decisively used in the synthesis of various organic compounds but also play a consequence role in natural product synthesis, modulation of biofilm formation, virulence and stress responses. In last few decades, an individual has witnessed considerable activity towards the synthesis of indole derivatives due to the possibilities for the design of polycyclic structures by the incorporation of multiple fused heterocyclic scaffolds in an attempt to achieve promising new heterocycles with chemical and biomedical relevance. Whereas, coumarin is a 2-oxo-2H-1-benzopyran and, also, have a wide range of application in the pharmaceutical field. In this review, we provide an overview of the synthesis of coumarin and indoles and their pharmacological evolution. The coumarin was synthesized using phenols, salicylaldehyde, benzaldehyde, phenylacetate, styrenes, and cinnamic acid with different catalyst and photocatalyst to give the best yield. Similarly, Indoles were synthesized iodobenzoic acid, alkynes, amines, alcohols, Nitrobenzaldehyde with the different catalyst under conventional and irradiation method. The effect of various catalytic medium, solvents and operational condition are discussed for obtaining the best yield. A comparative account of various reaction pathways like one-pot synthesis (Multicomponent reaction) and the multistep reaction of coumarin and indoles are discussed. INTRODUCTION: Coumarins belong to a large family of heterocyclic compounds with a benzo-apyrone moiety, of natural and synthetic origin. Coumarin is the most representative molecule are widely distributed in plants like tonka bean (Dipteryx odorata Wild). It has been extensively used in biochemical and pharmaceutical fields 1 .

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Benzenesulfonic Acid: A Versatile Catalyst for the Synthesis of Bis(indolyl)methanes as Antioxidants

Cited by 12 publications

References 21 publications

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

Brønsted Acidic Ionic Liquid Catalyzed Three-Component Friedel–Crafts Reaction for the Synthesis of Unsymmetrical Triarylmethanes

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