Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

Hrizi, Asma; Cailler, Manon; Carcenac, Yvan; Thibonnet, J.

doi:10.3390/molecules26175287

Molecules

2021

DOI: 10.3390/molecules26175287

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Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

Asma Hrizi

Manon Cailler

Yvan Carcenac

et al.

Abstract: An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri- and tetra-substituted indole-2-carbonitriles.

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2024

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Cited by 2 publications

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Rh-Catalyzed C–H Alkynylation of Indole Derivatives with Silver(I)-Controlled Regiodivergence

Zhao,

Li,

Zhou

et al. 2024

Org. Lett.

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We have disclosed silver(I)-induced switching of regioselectivity in rhodium-catalyzed C−H alkynylation of indole derivatives with the help of a pivaloyl directing group by tuning C−H metalation modes. The judicious choice of AgOAc, Ag 2 O, and Ag 2 CO 3 affords an array of C2-alkynylated indoles, C4-alkynylated indoles, and C2,C4-dialkynylated indoles, respectively. The synthetic utility of the alkyne fragment is demonstrated by derivatization into valuable indole-based compounds.

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Rh-Catalyzed C–H Alkynylation of Indole Derivatives with Silver(I)-Controlled Regiodivergence

Zhao,

Li,

Zhou

et al. 2024

Org. Lett.

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Low-Molecular-Weight Synthetic Antioxidants: Classification, Pharmacological Profile, Effectiveness and Trends

Stoia

Oancea

2022

Antioxidants

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Mounting research has been performed and published on natural antioxidants, more so than on synthetic ones, as key molecules that control oxidative damage and its pathway to disease. Since the discovery of vitamins, various fully synthetic or natural-identical compounds have been developed as stable small molecules translated into constantly active and completely controlled products which are widely exploited in the food and pharmaceutical industries. There is currently a debate within the literature about their mechanism of action, bioavailability, safety and real benefit for human health. Using a semiquantitative method and eligible criteria of selection, this review aimed to provide a very useful classification of antioxidants and a comprehensive cross-disciplinary description of 32 approved synthetic/natural-identical antioxidants, in terms of regulatory, antioxidant mechanism of action, safety issues, pharmacological properties, effectiveness in human health, timeline and future trends. Enriched interpretation of the data was obtained from summary bibliometrics, useful to portray the “good antioxidant” within the period 1966–2021 and, hopefully, to encourage further research.

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Synthesis of New Highly Functionalized 1H-Indole-2-carbonitriles via Cross-Coupling Reactions

Cited by 2 publications

References 56 publications

Rh-Catalyzed C–H Alkynylation of Indole Derivatives with Silver(I)-Controlled Regiodivergence

Rh-Catalyzed C–H Alkynylation of Indole Derivatives with Silver(I)-Controlled Regiodivergence

Low-Molecular-Weight Synthetic Antioxidants: Classification, Pharmacological Profile, Effectiveness and Trends

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