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

RSC Advances, Год журнала: 2020, Номер 10(35), С. 20784 - 20793

Опубликована: Янв. 1, 2020

Recently, quinoline has become an essential heterocyclic compound due to its versatile applications in the fields of industrial and synthetic organic chemistry. It is a vital scaffold for leads drug discovery plays major role field medicinal Nowadays there are plenty articles reporting syntheses main functionalization biological pharmaceutical activities. So far, wide range synthesis protocols have been reported literature construction this scaffold. For example, Gould-Jacob, Friedländer, Pfitzinger, Skraup, Doebner-von Miller Conrad-Limpach well-known classical used up now principal Transition metal catalysed reactions, metal-free ionic liquid mediated ultrasound irradiation reactions green reaction also useful compound. The part review focuses on highlights above-mentioned procedures findings tackle drawbacks side effects environment. Furthermore, various selected quinolines derivatives with potential activities will be presented.

Язык: Английский

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Recent Advances in the Synthesis of C2‐Functionalized Pyridines and Quinolines Using N‐Oxide Chemistry

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(1), С. 2 - 39

Опубликована: Окт. 12, 2020

Abstract While remarkable progress has recently been made for the direct C−H‐functionalization of azines, its application is still limited by a lack accessible functional groups (primarily carbon‐based) and poor regioselectivity. In contrast, C2‐functionalized pyridines quinolines can be easily synthesized treating readily available N ‐oxides with various reagents under appropriate activation conditions. This review seeks to comprehensively document synthetic methods introducing at C2 position quinolines. this work, we highlight recent developments in C2‐functionalization pyridine quinoline address both mechanisms regioselectivity reactions. We also describe pathways reactive species involved these processes number medically relevant nitrogen heteroaromatics. magnified image

Язык: Английский

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Metal-free C3-alkoxycarbonylation of quinoxalin-2(1H)-ones with carbazates as ecofriendly ester sources

Science China Chemistry, Год журнала: 2019, Номер 62(4), С. 460 - 464

Опубликована: Март 7, 2019

Язык: Английский

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Bromide-Promoted Visible-Light-Induced Reductive Minisci Reaction with Aldehydes

ACS Catalysis, Год журнала: 2019, Номер 10(1), С. 154 - 159

Опубликована: Ноя. 27, 2019

Radical addition is a robust tool for bond formation. While ketyl radical reactivity of aldehydes by photoredox has been well-established, herein, we have now revealed pathway umpolung with or without external reductant. Hence, the reductive alkylations and challenging benzylations nitrogen heteroarenes (i.e., Minisci reactions) are enabled bromide-promoted visible light-mediated photocatalysis. The present protocol offers mild, viable method late-stage transition-metal-free biologically active nitrogen-heteroarene molecules. Mechanistic studies indicative bromide-initiated acyl mechanism in absence

Язык: Английский

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Natural Deep Eutectic Solvent-Catalyzed Selenocyanation of Activated Alkynes via an Intermolecular H-Bonding Activation Process

ACS Sustainable Chemistry & Engineering, Год журнала: 2019, Номер 7(2), С. 2169 - 2175

Опубликована: Янв. 10, 2019

By employing cheap and biodegradable natural deep eutectic solvent as the catalyst reaction media, selective selenocyanation of activated alkynes via an intermolecular H-bonding activation pathway has been achieved, which allows for efficient construction various Z-vinyl selenolates.

Язык: Английский

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Photoredox-Catalyzed Sulfonylation ofO-Acyl Oximes via Iminyl Radicals with the Insertion of Sulfur Dioxide

Organic Letters, Год журнала: 2019, Номер 21(13), С. 4950 - 4954

Опубликована: Июнь 10, 2019

A multicomponent sulfonylation of O-acyl oximes via iminyl radicals with the insertion sulfur dioxide under photoredox catalysis is achieved. This reaction oximes, potassium metabisulfite, alkenes, and nucleophiles visible-light irradiation efficient, giving rise to a range sulfones in moderate good yields. broad scope presented functional group compatibility.

Язык: Английский

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Metal-catalyzed radical-type transformation of unactivated alkyl halides with C–C bond formation under photoinduced conditions

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(13), С. 2183 - 2199

Опубликована: Янв. 1, 2019

Recent advances in the metal-catalyzed radical-type transformation of unactivated alkyl halides with C–C bond formation under photoinduced conditions are summarized. Usually, a broad reaction scope is observed including tertiary, secondary, and primary halides, good functional group compatibility.

Язык: Английский

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Photoredox-catalyzed hydrosulfonylation reaction of electron-deficient alkenes with substituted Hantzsch esters and sulfur dioxide

Chemical Communications, Год журнала: 2019, Номер 55(43), С. 6010 - 6013

Опубликована: Янв. 1, 2019

A sulfonylation reaction of 4-substituted Hantzsch esters, DABCO·(SO2)2, and electron-deficient alkenes at room temperature in the presence photoredox catalysis under visible light irradiation is described. Not only (E)-chalcones but also (vinylsulfonyl)benzene 2-vinylpyridine are all suitable substrates transformation. This mild conditions shows a broad substrate scope with good functional group compatibility. plausible mechanism proposed, which that esters would be radical reservoirs catalysis. The alkyl generated situ from ester trapped by sulfur dioxide to produce an alkylsulfonyl radical, then undergo further transformation leading final outcome.

Язык: Английский

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Metal-free difunctionalization of alkynes leading to alkenyl dithiocyanates and alkenyl diselenocyanates at room temperature

Organic & Biomolecular Chemistry, Год журнала: 2018, Номер 16(46), С. 9064 - 9068

Опубликована: Янв. 1, 2018

A simple and practical method for the synthesis of alkenyl dithiocyanates diselenocyanates has been developed via stereoselective difunctionalization alkynes with NaSCN or KSeCN at room temperature. Through this methodology, a series could be efficiently conveniently obtained in moderate to good yields under mild metal-free conditions by use oxone PhI(OAc)2 as oxidants.

Язык: Английский

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Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

European Journal of Organic Chemistry, Год журнала: 2019, Номер 2020(10), С. 1274 - 1287

Опубликована: Май 3, 2019

Recent advances in the photoinduced sulfonylation reactions through insertion of sulfur dioxide are summarized. Among approaches developed reactions, via radical process can be accomplished with assistance photoredox catalysis presence visible light or under ultraviolet irradiation, depending substrates used reactions. Under conversion completed metal‐ and additive‐free conditions. It is noteworthy that alkyl halides possessing eliminable β‐hydrogen atom effective as precursors dioxide. Two parts, according to reaction pathways, introduced: (a) photo‐initiated formation subsequent capture dioxide; (b) photo‐assisted single electron transfer (SET) after During transformation, an oxidative reductive would occur catalysis.

Язык: Английский

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