Nature-derived Quinolines and Isoquinolines: A Medicinal Chemistry Perspective

Gupta, Mohit; Patel, Saloni

doi:10.2174/2215083805666190614115701

CTM

2021

DOI: 10.2174/2215083805666190614115701

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Nature-derived Quinolines and Isoquinolines: A Medicinal Chemistry Perspective

Mohit Gupta

Saloni Patel

Abstract: : Quinoline and isoquinoline motifs are commonly encountered in natural products of diverse origins. These moderately basic fused-heterocyclic rings containing natural products are adorned with remarkable biological activities with clinical use in various diseases demonstrating nature elegance and creativity. Therefore, these privileged rings have attracted profound interest from the scientific community. In this review, we have discussed medicinal chemistry perspective of the natural products containing quino… Show more

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Cited by 4 publications

References 96 publications

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An Oxidative S_N^H Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

Larin,

Avakyan,

Demidov

et al. 2024

Eur J Org Chem

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A novel and efficient method for the synthesis of 2‐alkylamino and 2‐dialkylamino derivatives of N‐oxides of 5‐, 6‐, 7‐ and 8‐nitroquinolines, which can potentially exhibit biological activity, as containing a pharmacophoric quinoline fragment, is described herein. The reactions of 5(6,7,8)‐nitroquinoline N‐oxides with various primary or secondary amines in the presence of potassium ferricyanide at in aqueous dioxane medium afforded the corresponding secondary and tertiary amines in moderate to excellent yields. This reaction is the first example of a Chichibabin reaction leading to the formation of 2‐alkylaminoquinoline derivatives at position 2 under mild conditions. A study of the antibacterial activity of some products was carried out.

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An Oxidative S_N^H Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

Larin,

Avakyan,

Demidov

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

Wang

Zhang

et al. 2023

J. Org. Chem.

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In this work, a mild and efficient catalyst-free α-allylation of 3,4-dihydroisoquinoline imines with Morita−Baylis− Hillman (MBH) carbonates was reported. The scopes of 3,4-dihydroisoquinolines and MBH carbonates as well as gram-scale synthesis were investigated, and densely functionalized adducts were obtained in moderate to good yields. The synthetic utility of these versatile synthons was further demonstrated by the facile synthesis of diverse benzo[a]quinolizidine skeletons.

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Iron-Catalyzed Oxidative Cyclization of 2-Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines

et al. 2023

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Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di-t-butyl peroxide. Then, the quinoline scaffold is synthesized through imine condensation/ radical cyclization/oxidative aromatization. Our protocol showed a broad substrate scope, and various functionalization and fluorescence applications of quinoline products demonstrated its synthetic ability.

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Nature-derived Quinolines and Isoquinolines: A Medicinal Chemistry Perspective

Cited by 4 publications

References 96 publications

An Oxidative S_N^H Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

An Oxidative S_N^H Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

Iron-Catalyzed Oxidative Cyclization of 2-Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines

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Nature-derived Quinolines and Isoquinolines: A Medicinal Chemistry Perspective

Cited by 4 publications

References 96 publications

An Oxidative SNH Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

An Oxidative SNH Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

Catalyst-Free α-Allylation of Dihydroisoquinolines with Morita–Baylis–Hillman Carbonates and Its Applications in the Construction of Benzo[a]quinolizidines

Iron-Catalyzed Oxidative Cyclization of 2-Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines

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Product

Resources

About

An Oxidative S_N^H Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium

An Oxidative S_N^H Alkylamination of 5(6,7,8)‐Nitroquinoline N‐Oxides in Aqueous Dioxane Medium