Ultrasonically Assisted Efficient and Green Protocol for the Synthesis of Bisindolylmethanes Using Malic Acid as a Homogeneous and Reusable Organocatalyst

Kasar, Sandeep B.; Thopate, Shankar R.

doi:10.2174/2213346105666180821114459

Cited by 8 publications

(6 citation statements)

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“…However, due to the sensitivity of some Lewis acids to water, they are gradually replaced by more stable and hydrophilic inorganic acids, ionic salts, ionic polymers, and so on. Among them, tetracationic acidic organic salts, [64] itaconic acid, [65] malic acid, [66] phospho-sulfonic acid, [67] thiamine hydrochloride, [68] and lactic acid [69] have been reported to be used in synthesizing BIMs. Recently, Loh et al realized the Friedel-Crafts-type reaction of indole with carbonyl compounds to access BIMs by employing Ph 3 C + [B(C 6 F 5 ) 4 ] À as a superacidic precatalyst and water as the reaction medium (Scheme 5).…”

Section: Alkylation Reactionsmentioning

confidence: 99%

Section: C−c Bond Forming Reactionsmentioning

confidence: 99%

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Recent Advances on Direct Functionalization of Indoles in Aqueous Media

Pang

Zuo

Zhang

et al. 2023

The Chemical Record

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Indoles and their derivatives have dominated a significant proportion of nitrogen‐containing heterocyclic compounds and play an essential role in synthetic and medicinal chemistry, pesticides, and advanced materials. Compared with conventional synthetic strategies, direct functionalization of indoles provides straightforward access to construct diverse indole scaffolds. As we enter an era emphasizing green and sustainable chemistry, utilizing environment‐friendly solvents represented by water demonstrates great potential in synthesizing valuable indole derivatives. This review aims to depict the critical aspects of aqueous‐mediated indoles functionalization over the past decade and discusses the future challenges and prospects in this fast‐growing field. For the convenience of readers, this review is classified into three parts according to the bonding modes (C−C, C−N, and C−S bonds), which focus on the diversity of indole derivatives, the prominent role of water in the chemical process, and the types of catalyst systems and mechanisms. We hope this review can promote the sustainable development of the direct functionalization of indoles and their derivatives and the discovery of novel and practical organic methods in aqueous phase.

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Section: Alkylation Reactionsmentioning

confidence: 99%

Section: C−c Bond Forming Reactionsmentioning

confidence: 99%

Recent Advances on Direct Functionalization of Indoles in Aqueous Media

Pang

Zuo

Zhang

et al. 2023

The Chemical Record

View full text Add to dashboard Cite

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Section: Few Examplesmentioning

confidence: 99%

“…This ambient-temperature protocol involved the reaction of indole and various aromatic aldehydes. 35…”

Section: Non-spiro 3-substituted Indolesmentioning

confidence: 99%

“…This ambient-temperature protocol involved the reaction of indole and various aromatic aldehydes. 35 Scheme 33 Synthesis of bis(indolyl)methanes using organocatalyst A series of bis(indolyl)methane derivatives 105a-o were prepared by the Deshmukh research group using pyruvic acid catalyst in water under ultrasonication (Scheme 34). 36 The authors synthesized 15 compounds by using this protocol and they compared all the US-promoted reactions with the conventional method.…”

Section: Review Synopen Scheme 32 Synthesis Of Bis(indolyl)methanesmentioning

confidence: 99%

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Recent Developments in Ultrasound-Promoted Aqueous-Mediated Greener Synthesis of Biologically Vital Indole Derivatives

Choupra

Aheer

Dandia

et al. 2023

SynOpen

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The extensive usefulness of N-heterocycles as potent bioactive motifs has attracted researchers to expand newer methods for their efficient synthesis. Particularly, indoles are widely known for their prevalent pharmacological properties. Green chemistry provides various facile synthetic tools viz. alternative energy resources, nonconventional solvents, nano-catalysts, etc. Modern strategies of using ultrasound waves as alternative energy resource in organic synthesis lead to the development of environment friendly and cost effective techniques. The chemical and mechanical effects of ultrasound waves impart significant enhancement in both stoichiometric and catalytic reactions. The exclusive physicochemical properties of water offer its widespread utility for carrying out organic reactions in it. The aim of this review article is to provide an inclusive summary of combined use of ultrasound and aqueous media for the facile synthesis of biologically vital indole derivatives.

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Humic Acid: A Promising and Green Bioorganic Catalyst in Organic Syntheses

Swaraj Acharya,

Bhusan Parida

2024

ChemistrySelect

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The growing pollution and threat to the environment demand green synthetic methods. Green chemistry mainly focuses on minimizing the waste and utilization of green solvents, energy sources, and catalysts and prefers one‐pot reactions. In this context, humic acid (HA), a natural bioorganic catalyst found in rivers, peat coal and sewage; is a high molecular weight macromolecule containing multifunctional groups, mainly contains quinone, phenolic OH, and COOH groups which make it acidic and activate carbonyl groups by protonation. Owing to its green aspect such as biodegradability, recyclability and reusability, humic acid is considered as sustainable bioorganic catalyst which meets the criteria for industrial requirements. The HA is mild acidic in nature, thus many functional groups tolerate in the HA catalyzed reactions. After few initial reports in 2001 and 2009, the HA catalyzed reactions gained much attention by the organic synthetic community from 2019 in aldol condensation, Knoevenagel condensation, Claisen‐Schmidt reaction, Michael addition, Strecker synthesis, tetrazole synthesis, Hantzsch dihydropyridine synthesis, hydrosilylation of terminal alkenes, hydrogenation, α‐aminophosphonate synthesis, cross coupling reactions such as Heck and Suzuki coupling reactions. Herein we report the comprehensive analysis on the role of HA in organic transformations providing diverse array of molecular scaffolds till date and future perspective.

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Ultrasonically Assisted Efficient and Green Protocol for the Synthesis of Bisindolylmethanes Using Malic Acid as a Homogeneous and Reusable Organocatalyst

Cited by 8 publications

References 0 publications

Recent Advances on Direct Functionalization of Indoles in Aqueous Media

Recent Advances on Direct Functionalization of Indoles in Aqueous Media

Recent Developments in Ultrasound-Promoted Aqueous-Mediated Greener Synthesis of Biologically Vital Indole Derivatives

Humic Acid: A Promising and Green Bioorganic Catalyst in Organic Syntheses

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