Diversity‐Oriented Synthesis of Complex Pyrrole‐Based Architectures from Very Simple Starting Materials

Leonardi, Marco; Estévez, Verónica; Villacampa, Mercedes; Menéndez, J. Carlos

doi:10.1002/adsc.201900044

Cited by 15 publications

(3 citation statements)

References 99 publications

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“…Despite the high selectivity of this reaction to achieve a single compound, generally, due to the difficulties of isolating molecules formed by opposing side reactions, a low yield has been noticed. [57] The method has therefore been investigated using novel techniques, such as solvent-free settings, highspeed vibration milling, and a mixer operating at 20 Hz, this method afforded higher yields of pyrrole. [58] The pyrrole synthesis performed in solid phase conditions using acetoacetylated rink resin, synthesizing pyrrole-3-carboxamide derivatives (Scheme 1c) which resulted in the product isolation with high purity.…”

Section: Hantzsch Pyrrole Synthesismentioning

confidence: 99%

Pyrrole: A Decisive Scaffold for the Development of Therapeutic Agents and Structure‐Activity Relationship

Ganesh,

Raj,

Aruchamy

et al. 2023

ChemMedChem

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An overview of pyrroles as distinct scaffolds with therapeutic potential and the significance of pyrrole derivatives for drug development are provided in this article. It lists instances of naturally occurring pyrrole‐containing compounds and describes the sources of pyrroles in nature, including plants and microbes. It also explains the many conventional and modern synthetic methods used to produce pyrroles. The key topics are the biological characteristics, pharmacological behavior, and functional alterations displayed by pyrrole derivatives. It also details how pyrroles are used to treat infectious diseases. It describes infectious disorders resistant to standard treatments and discusses the function of compounds containing pyrroles in combating infectious diseases. Furthermore, the review covers the uses of pyrrole derivatives in treating non‐infectious diseases and resistance mechanisms in non‐infectious illnesses like cancer, diabetes, and Alzheimer's and Parkinson's diseases. The important discoveries and probable avenues for pyrrole research are finally summarized, along with their significance for medicinal chemists and drug development. A reference from the last two decades is included in this review.

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Section: Hantzsch Pyrrole Synthesismentioning

confidence: 99%

Pyrrole: A Decisive Scaffold for the Development of Therapeutic Agents and Structure‐Activity Relationship

Ganesh,

Raj,

Aruchamy

et al. 2023

ChemMedChem

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“…Various motifs of dicarbonyl compounds have been extensively utilized toward pyrrole synthesis. [83][84][85][86][87][88][89][90][91][92][93] As discussed in this section, this class of starting materials have enabled the development of a broad array of new synthetic reactions.…”

Section: Dicarbonyl Compoundsmentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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This review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle that can be found in numerous compounds of biological and material significance. Given its vast importance, pyrrole continues to be an attractive target for the development of new synthetic reactions. The contents of this article are organized by the starting materials, which can be broadly classified into four different types: substrates bearing π-systems, substrates bearing carbonyl and other polar groups, and substrates bearing heterocyclic motifs. Brief discussions on plausible reaction mechanisms for most transformations are also presented.1 Introduction2 From π-Systems2.1 Alkenes2.2 1,6-Dienes2.3 Allenes2.4 Alkynes2.5 Propargylic Groups2.6 Homopropargylic Amines3 From Carbonyl Compounds3.1 Aldehydes3.2 Ketones3.3 Cyanides and Isocyanides3.4 Formamides3.5 β-Enamines3.6 Dicarbonyl Compounds4 From Polar Compounds4.1 Aminols4.2 Diols4.3 Organonitro Compounds5 From Heterocycles5.1 Münchnones5.2 Isoxazoles5.3 Carbohydrates5.4 trans-4-Hydroxy-l-prolines5.5 Pyrrolines6 Summary

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“…14 In this sense, Guo et al described the synthesis of pyrrolo[1,2c]quinazolines via Cu(I)-catalyzed intramolecular cyclization of indolyl derivatives (Scheme 1a), 15 whereas Leonardi et al reported the Cu(II)-catalyzed cross-coupling reaction between aryl iodides and benzylamines followed by cyclization to afford the corresponding pyrroloquinazolines (Scheme 1b). 16 Moreover, Georgescu et al developed a three-component protocol for the synthesis of pyrrolo[1,2-c]quinazolines, in moderate yields under MW irradiation, through in situ formation of quinazolinium N-ylide, which undergoes a 1,3-dipolar cycloaddition with activated alkynes (Scheme 1c). 17 We have previously reported a Cu(I)-catalyzed one-pot Michael addition/dehydration cascade reactions, using βnitroolefins and 2-methyl-azaarenes, furnishing 3-(N-heteroarenyl)acrylonitriles and pyrrolo[1,2-c]quinazolines as minor products.…”

Section: ■ Introductionmentioning

confidence: 99%

Copper-Catalyzed Synthesis of Pyrrolo[1,2-c]quinazolines and Pyrrolo[2,1-a]isoquinolines and Antiplasmodial Evaluation

Moreira,

de Miranda,

dos Santos

et al. 2023

J. Org. Chem.

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Reactions involving C(sp 3 )−H bonds of azaarenes have been widely studied in recent years as they allow direct functionalization of these N-heterocycles without the use of harsh reaction conditions. In this work, we describe the C(sp 3 )−H functionalization of 4-methylquinazolines and 1-benzylisoquinolines, employing α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate. Under the optimized condition, 21 pyrrolo[1,2-c]quinazolines, as well as an imidazo[1,2-c]quinazoline and 4 pyrrolo[2,1-a]isoquinolines, were obtained in moderate to good yields. Furthermore, the biological activity of the pyrrolo[1,2c]quinazolines was evaluated against Plasmodium falciparum, and promising results were obtained.

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Diversity‐Oriented Synthesis of Complex Pyrrole‐Based Architectures from Very Simple Starting Materials

Cited by 15 publications

References 99 publications

Pyrrole: A Decisive Scaffold for the Development of Therapeutic Agents and Structure‐Activity Relationship

Pyrrole: A Decisive Scaffold for the Development of Therapeutic Agents and Structure‐Activity Relationship

Recent Advancements in Pyrrole Synthesis

Copper-Catalyzed Synthesis of Pyrrolo[1,2-c]quinazolines and Pyrrolo[2,1-a]isoquinolines and Antiplasmodial Evaluation

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