Iodine catalyzed four-component reaction: a straightforward one-pot synthesis of functionalized pyrroles under metal-free conditions

Reddy, G. Rajeshwar; Reddy, T. Raghunadha; Joseph, Suju C.; Reddy, K. Sateesh; Pal, Manojit

doi:10.1039/c2ra00982j

Cited by 61 publications

(13 citation statements)

References 28 publications

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“…Pal et al [26] reported an iodine-catalyzed four-component reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes affording polysubstituted pyrroles 3 under a metal-free condition. This is the first example of Grob and Camenisch's pyrrole synthesis [27] catalyzed by iodine via one-pot four-component reaction (Scheme 10.2).…”

Section: Pyrrolesmentioning

confidence: 99%

Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds

Dandia

Gupta

Maheshwari

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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The synthetic uses of molecular iodine are described. This chapter discusses the versatile uses of iodine in heterocyclic synthesis. Iodine is a universal oxidizing agent, a mild and nontoxic Lewis acid catalyst, and it catalyzes various organic reactions with high efficiency and selectivity. Also, iodine acts as an electrophile-nucleophile dual activator in the reactions. Further applications are the introduction of protecting groups, deprotection, iodocyclization, C-C bond formation, and formation of heterocycles. It is quite clear from the growing number

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Section: Pyrrolesmentioning

confidence: 99%

Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds

Dandia

Gupta

Maheshwari

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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“…Based on the literature [9,10], we have proposed a plausible mechanism for the one-pot reaction (Scheme 5).…”

Section: Multicomponent Synthesis Of Pyrroles By Variousmentioning

confidence: 99%

“…us, this straightforward approach could be an environmentally friendly and economical alternative to modern organic synthesis and combinatorial and medicinal chemistry [8]. Recently, a new four-component reaction employing 1,3dicarbonyl compounds, amines, aldehydes, and nitroalkanes to synthesize tetra-substituted pyrroles derivatives has been performed using FeCl 3 [9], iodine [10], NiCl 2 ·6H 2 O [11], [HBim]BF 4 [12], and silica tungsten acid (STA) [13]. However, these methods use toxic metals as homogeneous catalysts which are not recyclable, and although ionic liquids are considered as a mild and environmentally friendly solvent in modern organic chemistry [14], the presence of impurities can greatly affect their physicochemical properties [15], and their toxicities are not well known [16].…”

Section: Introductionmentioning

confidence: 99%

Natural Hydroxyapatite: Green Catalyst for the Synthesis of Pyrroles, Inhibitors of Corrosion

Louroubi

Nayad

Hasnaoui

et al. 2021

Journal of Chemistry

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Polysubstituted pyrroles have been synthesized in good yields via a four-component one-pot reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes using natural hydroxyapatite (HAp) as an efficient green catalyst. This strategy provides advantages such as simple experimental and work-up procedures, mild conditions, high selectivity, low cost, high atom economy, and environmental friendliness; it uses a green commercial catalyst and does not require a solvent. The electrochemical behavior of S300 steel in 1 M hydrochloric acidic was studied in the presence of these heterocyclic compounds. The results showed good inhibition efficiency for steel in acidic media.

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“…Recently, substituted pyrroles have been produced by MCR methods using different catalysts such as FeCl 3 , gluconic acid, NiCl 2 .6H 2 O, CeCl 3 .7H 2 O, and p‐toluenesulfonic acid doped polystyrene (PS‐PTSA) . Although these catalysts are very useful, they have limitations such as low product yields, being unrecyclable, and need long reaction times. A developing class of catalysts, which are nowadays of growing interest are those from bioresources.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Multicomponent Synthesis of Substituted Pyrroles by using Chitosan as an Organocatalyst

2018

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The solvent‐free synthesis of substituted pyrroles in high yields using chitosan as a green, recyclable, and reusable catalyst has been described. This multicomponent protocol includes the reaction of aldehydes, amines, 1,3‐dicarbonyl compounds, and nitromethane. The use of a green, biodegradable, environmentally benign, and available catalyst along with its high activity in a four‐component reaction (4CR) makes this method an efficient alternative route to substituted pyrroles. The catalyst can be recycled and reused for several times, without a considerable loss in its activity.

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Iodine catalyzed four-component reaction: a straightforward one-pot synthesis of functionalized pyrroles under metal-free conditions

Cited by 61 publications

References 28 publications

Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds

Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds

Natural Hydroxyapatite: Green Catalyst for the Synthesis of Pyrroles, Inhibitors of Corrosion

One‐Pot Multicomponent Synthesis of Substituted Pyrroles by using Chitosan as an Organocatalyst

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