Cp*Co(III)‐Catalyzed Dehydrative C2‐Prenylation of Pyrrole and Indole with Allyl Alcohols

Suchand, Basuli; Sahu, Samrat; Saha, Shuvendu; Maji, Modhu Sudan

doi:10.1002/adsc.202100811

Cited by 16 publications

(6 citation statements)

References 81 publications

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“…Prenylating reagent plays a significant function in bioactive and synthetic substances because it has a high binding affinity for proteins and increases membrane permeability, enhancing bioactivity and bioavailability of prenylated drugs. Through a specific prenyl-binding domain, the prenyl group plays an important role in proteinprotein binding [22,23].…”

Section: Reagents For Prenylation Reaction and Their Applicationsmentioning

confidence: 99%

Protein Prenylation and Their Applications

Surana¹,

Pawar²,

Khairnar³

et al. 2024

Modifications in Biomacromolecules

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Prenylation is a universal covalent post-translational modification found in all eukaryotic cells, comprising attachment of either a farnesyl or a geranylgeranyl isoprenoid. Prenyl group is important for protein-protein binding through specialized prenyl-binding domains. Farnesylation and geranyl geranylation are very important in C-terminal anchoring of proteins to the cell membrane. These post-translational modification are most often catalyzed by either protein farnesyl transferase (FTase) or protein geranyl geranyl transferase-I (GGTase-I). These enzymes typically recognize a CaaX motif, where “C” is the cysteine to be prenylated and the remainder of the motif leads to recognition by FTase and/or GGTase-I. Prenylation plays vital role in diversification of natural products flavonoids, coumarins, and isoflavonoids. Many prenylated compounds have been identified as active components in medicinal plants with biological activities, such as anti-cancer, anti-spasmodic, anti-bacterial, anti-fungal, anti-inflammatory, and anti-androgen activity. Due to their beneficial effects on diseases, prenylated compounds are of particular interest as lead compounds for producing drugs and functional foods. In this chapter, we concise the prenylation reactions of aromatic compounds such as indole, ketones, and aldehydes that may results to lead molecules discovery. Prenylation reactions are applied on azoles, anilines, thioles, indole, α-carbonyl bromides, and aryl bromide. There are several drugs that are obtained from prenylation, i.e. (-)-17-hydroxy-citrinalin, (+)-stephacidin, prenylated. In this text there is no referencing, it is a chemical name, so keep as it is.

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Section: Reagents For Prenylation Reaction and Their Applicationsmentioning

confidence: 99%

Protein Prenylation and Their Applications

Surana¹,

Pawar²,

Khairnar³

et al. 2024

Modifications in Biomacromolecules

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“…[16] Later, the scope was expanded to allylation of benzamides and 6-arylpurines, [17] as well as indoleand pyrrolecarbothioamides. [18] Related examples of allylation of arenes with tertiary allyl amines [19] and with fluorinated alkenes [20] have been also described. In these cases, the mechanism would proceed via CÀ H metalation, alkene insertion, and β-heteroatom-elimination, which would be detrimental to the atom economy of the reactions.…”

Section: Introductionmentioning

confidence: 99%

“…Matsunaga and Kanai demonstrated that unactivated allyl alcohols can also be used in the allylation reaction of N ‐(pyrimidin‐2‐yl)‐1 H ‐indoles [16] . Later, the scope was expanded to allylation of benzamides and 6‐arylpurines, [17] as well as indole‐ and pyrrolecarbothioamides [18] . Related examples of allylation of arenes with tertiary allyl amines [19] and with fluorinated alkenes [20] have been also described.…”

Section: Introductionmentioning

confidence: 99%

Directed C−H Allylation of Aromatic Carboxamides with Allyl Aryl Ethers under Cp*Co(III)‐Catalysis

Carral‐Menoyo,

Barbolla,

Santiago

et al. 2023

Eur J Org Chem

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The Cp*Co(III) C−H allylation of (hetero)arenes with allyl aryl ethers has been developed using an amide as directing group (24 examples). DFT calculations have shed light on the mechanistic course and reactivity pattern, showing that strong electron releasing groups favour the reaction by reducing the activation barrier of the rate‐determining C−H activation step. However, the steric strain can increase the energy of the migratory insertion step to the point of completely preventing the reaction, as in the case of the 3,5‐dimethylbenzamide. The obtained allylated compounds have been transformed into a variety of interesting heterocyclic and carbocyclic structures, such as isoquinolones and isochromanones.

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“…Moreover, C2 substituted indoles are also ubiquitous in various natural products and pharmaceuticals . Recently, transition-metal-catalyzed directed indoles C2 alkylation with alkenes has been developed but without reports on conjugated alkenes. In consideration of the importance of these alkynyl- and indole-containing molecules, we hope to develop an efficient method to achieve three-component cross-coupling of conjugated alkenes with electrophilic alkynylating reagent and indoles (Scheme C).…”

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confidence: 99%

Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes with Indoles Using Ethynylbenziodazolones as Electrophilic Alkynylating Reagents

Huang

Chen

2022

Org. Lett.

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A palladium-catalyzed regioselective 1,2-alkynyl-carbonalization of conjugated dienes with ethynylbenziodazolone (EBZ) and indoles has been developed for the first time. Various molecules containing alkenyl, alkynyl, and indole groups were readily obtained. Moreover, the resulting products can be applied to various derivatizations. This protocol uses EBZ as an electrophilic alkynylating reagent, avoiding the byproduct of dimerization of alkynes.

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Cp*Co(III)‐Catalyzed Dehydrative C2‐Prenylation of Pyrrole and Indole with Allyl Alcohols

Cited by 16 publications

References 81 publications

Protein Prenylation and Their Applications

Protein Prenylation and Their Applications

Directed C−H Allylation of Aromatic Carboxamides with Allyl Aryl Ethers under Cp*Co(III)‐Catalysis

Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes with Indoles Using Ethynylbenziodazolones as Electrophilic Alkynylating Reagents

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