Synthesis of substituted pyrroles via Amberlyst-15 mediated MCR under ultrasound

Murthi, P. Radha Krishna; Rambabu, D.; Rao, Mandava V. Basaveswara; Pal, Manojit

doi:10.1016/j.tetlet.2013.11.073

Cited by 38 publications

(3 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2010, a paper described the preparation of highly functionalized pyrroles by combining 1,3-dicarbonyl compounds, amines, aromatic aldehydes, and nitroalkanes in the presence of FeCl 3 as a catalyst [76]. This method presents some drawbacks such as low yields and tedious work-up procedures, with other catalytic methodologies being developed with better yields using transition metals [77] or other non-metallic catalysts [78]. All the processes described required long reaction times.…”

Section: Dess As Catalysts In Multicomponent Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents as Catalysts in the Synthesis of Active Pharmaceutical Ingredients and Precursors

Falcini,

Gonzalo

2024

Catalysts

View full text Add to dashboard Cite

Deep Eutectic Solvents (DESs) have appeared in recent years as an appealing alternative to classical organic solvents, due to their valuable environmental properties. In addition, these compounds, formed by the combination of one hydrogen bond donor with a hydrogen bond acceptor at a defined stoichiometric ratio, present other valuable activities not only as a reaction medium. DESs can also be employed as catalysts through hydrogen-bond interactions in different chemical transformations, thus substituting hazardous reagents and solvents. The search for novel and more environmentally friendly catalysts is an area of interest of pharmaceutical chemists, and therefore, the efforts made in the application of DESs as catalysts in the synthesis of APIs or its precursors are described, focusing mainly on condensations, nucleophilic additions to carbonyl moieties, and multicomponent reactions.

show abstract

Section: Dess As Catalysts In Multicomponent Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents as Catalysts in the Synthesis of Active Pharmaceutical Ingredients and Precursors

Falcini,

Gonzalo

2024

Catalysts

View full text Add to dashboard Cite

show abstract

“…The pyrrole nucleus can be found in many natural products, including complex macromolecules, such as porphyrins, heme, chlorophyll, chlorines, etc., that present important biological activities [160] . The Murthi group [161] has developed a simple procedure for the synthesis of these important heterocycles via four-component reaction mediated by Amberlyst-1 as catalyst under ultrasound, by condensation of aromatic aldehydes ( 1 ), β -ketoesthers ( 2 ), primary amines ( 17 ) and nitromethane ( 51 ), which acted as reactant as well as solvent ( Scheme 20 ). Due to the presence of acid and sulfonated groups on its surface, the resinous material Amberlyst 15 has been used successfully in heterogeneous catalysis to promote organic transformations [162] , [163] , [164] .…”

Section: Ultrasound-assisted Mcrs Under Heterogeneous Catalysismentioning

confidence: 99%

Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions

Machado

Santos

Januario

et al. 2021

Ultrasonics Sonochemistry

View full text Add to dashboard Cite

show abstract

“…An alternative method for pyrrole synthesis using electrochemical techniques has been reported [26] . Various catalysts, like nano‐NiFe 2 O 4 , [27] nano‐NiO, [28] tungsten complex, [29] amberlyst‐15, [30] nano CoFe 2 O 4 supported antimony (III)catalyst, [31] Heterogeneous Fe‐MIL‐101 catalysts, [32] nano CuO catalyst [33] and [NMPH]CH 3 SO 3 [34] have been utilized for the synthesis of substituted pyrroles. There are several synthetic procedures reported for the synthesis of polysubstituted pyrroles providing flexibility based on the starting ingredients and desired end products [35–38] .…”

Section: Introductionmentioning

confidence: 99%

Cu(I)‐Catalyzed Coupling Reactions of β‐Nitrostyrene, 1,3‐Dicarbonyl compound & Aryl amine: An Efficient Method For the Synthesis of Polysubstituted Pyrroles

Samal,

Pati

2024

ChemistrySelect

View full text Add to dashboard Cite

A convenient Cu(I) Catalyzed three‐component coupling strategy for the synthesis of polysubstituted pyrroles is developed using simple and readily available building blocks like, 1, 3‐dicarbonyl compound, aryl amine, and β‐nitrostyrene. CuI has been rarely explored for the pyrrole ring synthesis and a comparative analysis of our current catalyst with a range of previously reported catalysts suggested that, CuI is one of the best catalysts for the multicomponent synthesis of polysubstituted pyrrole derivatives. Notably, this process has several advantages, including a simple and practical set‐up with hassle free reaction conditions, extensive substrate scope, short reaction time, high atom economy and environmentally favorable approach. This methodology provides an alternative approach to the highly substituted pyrroles and under optimized reaction conditions, polysubstituted pyrroles were formed in good to excellent yields. Cu(I) catalyzed Mannich reactions followed by Michael addition reactions along with subsequent intramolecular cyclization are believed to be the key steps of this reaction process.

show abstract

Synthesis of substituted pyrroles via Amberlyst-15 mediated MCR under ultrasound

Cited by 38 publications

References 29 publications

Deep Eutectic Solvents as Catalysts in the Synthesis of Active Pharmaceutical Ingredients and Precursors

Deep Eutectic Solvents as Catalysts in the Synthesis of Active Pharmaceutical Ingredients and Precursors

Greener organic synthetic methods: Sonochemistry and heterogeneous catalysis promoted multicomponent reactions

Cu(I)‐Catalyzed Coupling Reactions of β‐Nitrostyrene, 1,3‐Dicarbonyl compound & Aryl amine: An Efficient Method For the Synthesis of Polysubstituted Pyrroles

Contact Info

Product

Resources

About