Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review

Weyesa, Abdanne; Mulugeta, Endale

doi:10.1039/d0ra03763j

Cited by 196 publications

(131 citation statements)

References 67 publications

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“…The arylation was found to be tolerant of various substituted substrates in moderate to good yields depending on the heteroarene. This late-stage C-2 arylation of these essential pharmacophores provided a practical strategy for the synthesis of attractive N -heterobiaryl derivatives that are widely found in pharmaceuticals and natural compounds, particularly in alkaloids [ 77 , 78 , 79 , 80 , 81 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Besson

Fruit

2021

Pharmaceuticals

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Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Besson

Fruit

2021

Pharmaceuticals

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“…The quinoline ring continues to occupy an important place in medicinal chemistry as a valuable scaffold, presenting in many natural and biologically active compounds [ 1 , 2 , 3 , 4 , 5 , 6 ]. The quinoline scaffold is an integral part of a variety of drugs, including antimalarial medications (chloroquine, hydroxychloroquine, amodiaquine and primaquine) and fluoroquinolone antibiotics (ciprofloxacin, levofloxacin, gatifloxacin and moxifloxacin).…”

Section: Introductionmentioning

confidence: 99%

Efficient Regioselective Synthesis of Novel Water-Soluble 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides

2021

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Regioselective synthesis of novel 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl sulfide) and tetravinyl silane. The novel reagent 8-quinolinesulfenyl bromide was used in the annulation reactions. The influence of the substrate structure and the nature of heteroatoms on the direction of the reactions and on product yields has been studied. The opposite regiochemistry was observed in the reactions with vinyl chalcogenides and tetravinyl silane. The obtained condensed heterocycles are novel water-soluble functionalized compounds with promising biological activity.

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“…The quinoline derivatives exhibit a variety of biological activities, including antibacterial, antifungal, anticancer, anti-inflammatory, antimalarial and antileishmanial actions [ 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. The fluoroquinolone antibiotics (ciprofloxacin, levofloxacin, gatifloxacin and moxifloxacin) and antimalarial medications (chloroquine, hydroxychloroquine, amodiaquine and primaquine) took an important place in pharmacotherapy.…”

Section: Introductionmentioning

confidence: 99%

Efficient Regioselective Synthesis of Novel Condensed Sulfur–Nitrogen Heterocyclic Compounds Based on Annulation Reactions of 2-Quinolinesulfenyl Halides with Alkenes and Cycloalkenes

2021

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The preparation of novel reagents 2-quinolinesulfenyl chloride and bromide based on available 2-mercaptoquinoline has been described. This approach opens up opportunities for the introduction of 2-quinolinesulfenyl chloride and bromide into organic synthesis. Regioselective synthesis of novel 1,2-dihydro[1,3]thiazolo[3,2-a]quinolin-10-ium derivatives in high yields has been developed by annulation reactions of 2-quinolinesulfenyl chloride and bromide with alkenes. Condensed tetracyclic products have been obtained by the reactions of 2-quinolinesulfenyl chloride and bromide with cycloalkenes. The opposite regiochemistry in the reactions with styrene, isoeugenol and 1-alkenes was discussed.

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Recent advances in the synthesis of biologically and pharmaceutically active quinoline and its analogues: a review

Abstract: Recently, quinoline has become an essential heterocyclic compound due to its versatile applications in the fields of industrial and synthetic organic chemistry.

Cited by 196 publications

References 67 publications

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

Efficient Regioselective Synthesis of Novel Water-Soluble 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides

Efficient Regioselective Synthesis of Novel Condensed Sulfur–Nitrogen Heterocyclic Compounds Based on Annulation Reactions of 2-Quinolinesulfenyl Halides with Alkenes and Cycloalkenes

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