A novel method for the synthesis of 3-aminoindoles using iodine and Cs2CO3 as catalyst

Muralidhar, Pamerla; Kumar, B. Santosh; Kerru, Nagaraju; Maddila, Suresh

doi:10.1016/j.cdc.2021.100731

Cited by 4 publications

(4 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As for the latter, the major strategies for introducing an amino group at the C3 indole position have remained the nitration [2,13,15,17,25,26] or azidation [18] reactions followed by a reduction to the free amine. The synthesis starts from the corresponding 3-indolecarboxylic acids by a twostep sequence involving the Curtius rearrangement [16,27], palladium-catalyzed amination of indole halides [28], as well as a number of some recent direct C-H amination methods [29][30][31][32][33][34], have been also reported. However, these transformations are mostly multistep processes that require subsequent protection-deprotection or functional group interconversion steps and often suffer from limited scope and efficacy.…”

Section: Introductionmentioning

confidence: 99%

A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

et al. 2023

View full text Add to dashboard Cite

A novel, low-cost method for the preparation of not easily accessible free 3-aminoindoles has been developed. This approach is based on a well-established reaction between indoles and nitrostyrene in the presence of phosphorous acid, which results in the formation of 4′-phenyl-4′H-spiro[indole-3,5′-isoxazoles]. The latter could be transformed to corresponding aminated indoles by reaction with hydrazine hydrate in good or excellent yields upon microwave-assisted heating.

show abstract

Section: Introductionmentioning

confidence: 99%

A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

et al. 2023

View full text Add to dashboard Cite

show abstract

“…For example, Seong and co-workers developed an efcient base-mediated synthetic method to access 3-aminoindoles from benzonitriles [22], Hu and coinvestigators used a rhodium-based catalyst for the electrophilic amidation of 2-alkynylanilines for the synthesis of 3-amidoindoles [23], while Matsuda et al reported on copper-catalysed annulative electrophilic amination of 2alkynylanilines to access 3-aminonindoles (Scheme 2) [24]. Recently, Muralidhar et al reported on the efcient one-pot iodine and caesium carbonate assisted synthesis of 3aminoindole derivatives [25]. Despite these advancements, more diversifed synthetic methods are needed to address the ever increasing demand 3-aminoindoles and the related heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Copper- and Ligand-Free Sonogashira Cross-Coupling: Access to Novel 3-Aminoindole Derivatives and Their Biological Evaluations

Rikhotso,

Poopedi,

Nxumalo

et al. 2023

Journal of Chemistry

View full text Add to dashboard Cite

Indole-containing compounds are widely distributed in the plant and animal kingdom, and their biological activity and pharmacological properties have prompted research into their chemical properties. This study developed a one-pot methodology for the synthesis of 3-aminoindole derivatives using copper- and ligand-free Sonogashira cross-coupling reaction conditions. The synthesised 3-aminoindole derivatives were confirmed using spectroscopic techniques. The resulting 3-aminoindole derivatives were biologically evaluated against Mycobacterium tuberculosis and Plasmodium falciparum. For example, indole derivatives 10a (7.813 µM) and 10j (8.332 µM) were the most active derivatives in the CAS and ADC media, respectively.

show abstract

“…Over the years, diverse transition metal oxide nanomaterials have been investigated as sustainable, recyclable catalysts for developing bioactive promising small organic molecules [ 16 , 17 , 18 ]. Thus, the research outcomes have showcased the path for designing novel nanomaterials and investigating the mechanism and reactivity to allow the new ideal routes of organic synthesis [ 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Progress in the Multicomponent Synthesis of Pyran Derivatives by Sustainable Catalysts under Green Conditions

2022

Self Cite

View full text Add to dashboard Cite

Pyrans are one of the most significant skeletons of oxygen-containing heterocyclic molecules, which exhibit a broad spectrum of medicinal applications and are constituents of diverse natural product analogues. Various biological applications of these pyran analogues contributed to the growth advances in these oxygen-containing molecules. Green one-pot methodologies for synthesising these heterocyclic molecules have received significant attention. This review focuses on the recent developments in synthesising pyran ring derivatives using reusable catalysts and emphasises the multicomponent reaction strategies using green protocols. The advantages of the catalysts in terms of yields, reaction conditions, and recyclability are discussed.

show abstract

A novel method for the synthesis of 3-aminoindoles using iodine and Cs2CO3 as catalyst

Cited by 4 publications

References 42 publications

A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

A Two-Step Synthesis of Unprotected 3-Aminoindoles via Post Functionalization with Nitrostyrene

Copper- and Ligand-Free Sonogashira Cross-Coupling: Access to Novel 3-Aminoindole Derivatives and Their Biological Evaluations

Recent Progress in the Multicomponent Synthesis of Pyran Derivatives by Sustainable Catalysts under Green Conditions

Contact Info

Product

Resources

About