Efficient, Three-Component Synthesis of Pyrrole Derivatives Catalyzed by Iodobenzene and Oxone

Jagadhane, Prashant B.; Jadhav, Nikhil C.; Herlekar, Omkar P.; Telvekar, Vikas N.

doi:10.1080/00397911.2015.1066392

Cited by 14 publications

(7 citation statements)

References 23 publications

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“…In this context, Jagadhane et al .reported a one‐pot three‐component synthesis for pyrrole derivatives 626 a – j from easily available amines, nitrostyrene 625 , and diketones 580 with the involvement of oxone in the presence of catalytic amount of iodobenzene and 4 Å molecular sieves (MS) in EtOH solvent under reflux condition (Scheme 193). [456] Captivatingly, this protocol has successfully been employed to assemble a wide range of pyrrole derivatives in moderate to good yields. On the other hand, quite recently, Ravichander's group revealed a new and facile synthesis of N ‐substituted pyrrole derivatives 628 a – c by means of Clauson‐Kaas reaction involving 2,5‐dimethoxytetrahydrofuran 627 with a variety of arylamines in the presence of oxone under microwave irradiation (Scheme 194).…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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“…12h i Apart from these reports, several multicomponent strategies emerged for the synthesis of polysubstituted pyrrole catalyzed by metals such as Rh, 13 W, 14 Fe, 15a In, 15b Zr, 16a Ce, 16b Au, 16c and Ni. 17 Nonmetal-catalysed MCR for the synthesis of substituted pyrroles were reported in the presence of molecular iodine, 18a iodobenzene and Oxone, 18b gluconic and aqueous solution (GAAS), 18c and graphite. 18d…”

Section: Table 1 Optimization Of Reaction Conditions Fo...mentioning

confidence: 99%

An Efficient One-Pot, Three-Component Synthesis of Tetrasubstituted Pyrroles under Catalyst- and Solvent-Free Conditions

Gnanaoli

Rajkumar

Nagarajan

et al. 2023

Synlett

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An environmentally benign, catalyst- and solvent-free, three-component synthesis of tetrasubstituted pyrroles was established. The reaction proceeds via a nucleophilic attack of primary amine on dialkyl acetylenedicarboxylate followed by Michael addition with β-nitro styrene and successive intramolecular cyclization and aromatization to yield 1,2,3,4-tetrasubstituted pyrroles in good to excellent yields. A wide range of primary amines including aromatic amines, benzyl amines were coupled with differently substituted β-nitro styrenes and dialkyl acetylenedicarboxylate. Furthermore, compared to previous reported methods, the present study is highly atom economical and environmentally benign and can be scaled up

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“…In 2015, three‐component synthesis of pyrroles using idobenzene and oxone as catalyst reported by Telvekar and co‐workers. For this purpose, amine (1 mmol), β ‐nitrostyrenes (1.1 mmol) and 1,3‐dicarbonyl compounds (1 mmol) in the presence of idobenzene and oxone was carried out in different solvents such as CH 3 CN/H 2 O (1 : 1), THF, CH 3 OH, DMF and EtOH that results shown EtOH is the best suitable solvent for this reaction and (1 mmol) of iodobenzene and (1.5 mmol) of oxone is the optimum amount (Scheme ) …”

Section: Synthesis Of Pyrrole Derivatives By β‐Nitrostyrene Via Multimentioning

confidence: 99%

Application of β‐Nitrostyrene in Multicomponent Reactions for the Synthesis of Pyrrole Derivatives

Rostami

Shiri

2020

ChemistrySelect

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β-nitrostyrene is an important and effective starting material for the synthesis of heterocycle compounds such as pyrrole derivatives via multicomponent reactions. β-nitrostyrene in its reactions undergoes Michael addition. Pyrroles derivatives are an important group of heterocycle compounds that have many biological and pharmacological activities and are exist in the structure many of natural products. Usually, synthesis of pyrrole derivatives by β-nitrostyrene performed through multicomponent reactions. In this review, synthesis of pyrroles derivatives by β-nitrostyrene through multicomponent reactions is discussed.

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Efficient, Three-Component Synthesis of Pyrrole Derivatives Catalyzed by Iodobenzene and Oxone

Cited by 14 publications

References 23 publications

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

An Efficient One-Pot, Three-Component Synthesis of Tetrasubstituted Pyrroles under Catalyst- and Solvent-Free Conditions

Application of β‐Nitrostyrene in Multicomponent Reactions for the Synthesis of Pyrrole Derivatives

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