Progress in the Chemistry of Tetrahydroquinolines

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(8), P. 5057 - 5191

Published: April 9, 2019

Tetrahydroquinoline is one of the most important simple nitrogen heterocycles, being widespread in nature and present a broad variety pharmacologically active compounds. This Review summarizes progress achieved chemistry tetrahydroquinolines, with emphasis on their synthesis, during period from mid-2010 to early 2018.

Language: Английский

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Calix[n]arenes and its derivatives as organocatalysts

Coordination Chemistry Reviews, Journal Year: 2022, Volume and Issue: 472, P. 214791 - 214791

Published: Sept. 2, 2022

Language: Английский

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Gold‐catalyzed [4+2] Annulations of Dienes with Nitrosoarenes as 4 π Donors: Nitroso‐Povarov Reactions

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(29), P. 9831 - 9835

Published: May 23, 2019

This work reports the first success of nitroso-Povarov reaction, involving gold-catalyzed [4+2] annulations nitrsoarenes with substituted cyclopentadienes. In this catalytic sequence, nitrosoarenes presumably attack gold-π-dienes by a 1,4-addition pathway, generating allylgold nitrosonium intermediates to complete an intramolecular cyclization. Acyclic dienes are also applicable substrates, and affording oxidative products.

Language: Английский

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The Povarov Reaction: A Versatile Method to Synthesize Tetrahydroquinolines, Quinolines and Julolidines

Synthesis, Journal Year: 2022, Volume and Issue: 54(14), P. 3162 - 3179

Published: March 10, 2022

Abstract The multicomponent Povarov reaction represents a powerful approach for the construction of substances containing N-heterocyclic frameworks. By using reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines single step, it is possible form following new bonds: two Csp 3–Csp 3 one 3–Nsp 3, 2–Csp 2 2–Nsp 2, four 1, respectively. This short review discusses main features including its mechanism, scope by employing different catalysts substrates, as well stereoselective versions. 1 Introduction Mechanism Reaction Tetrahydroquinolines 4 Quinolines 5 Julolidines 6 Concluding Remarks

Language: Английский

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Direct Construction of Julolidines via Reductive Annulation of Quinolines and Conjugated Enones by a MOF-Derived Hierarchically Porous Iridium Catalyst

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(16), P. 10294 - 10303

Published: Aug. 5, 2022

Here, we describe the development of a MOF-derived hierarchically porous ZrO2-supported iridium catalyst (Ir-N@HP-mesoZrO2), featuring sufficient accessible catalytic sites even with ultralow loading. Such was successfully applied to selective and direct construction julolidines via reductive annulation readily available quinolines conjugated enones, proceeding good substrate functional group compatibility, reusable catalyst, high step atom efficiency, easy applicability for fabrication molecules. The present work opens door further develop useful transformations by merging hydrogen transfer-mediated activation in situ incorporation coupling sequence under heterogeneous catalysis.

Language: Английский

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Green synthesis of furfural from xylose and corn cob biomass

Reaction Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 8(8), P. 1969 - 1980

Published: Jan. 1, 2023

Furfural is a versatile, high-value-added platform molecule that can be produced from five carbon atom (C5) carbohydrates present in lignocellulosic biomass.

Language: Английский

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Photomediated Radical Cascade Addition–Cyclization of N-Butenoyl Tetrahydroquinolines: Accessing Functionalized Julolidines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Herein, we describe the photomediated radical cascade addition-cyclization of N-butenoyl tetrahydroquinolines to access various functionalized julolidine-5-one. The scope methodology was illustrated with several sulfonyl chlorides and tetrahydroquinolines. Other precursors, such as trifluoromethyl, bromoacetonitrile, bromoacetates, etc., also worked efficiently, demonstrating broad utility method. Finally, large-scale synthesis sulfonyl-substituted julolidine-5-one downstream conversions synthesized julolidine derivatives were carried out illustrate synthetic methodology.

Language: Английский

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Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

European Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 2019(27), P. 4273 - 4310

Published: June 26, 2019

Julolidines constitute a class of N ‐heterocycle compounds which have in common the 2,3,6,7‐tetrahydro‐1 H ,5 ‐benzo[1,2]quinolizine ring. Due mainly to its fluorescence properties, such structures shown potential application range scientific and technological areas attracted attention great variety research groups. For example, julolidines been used for detection ions volatile environmental biological samples, construction dye‐sensitized solar cells, photoconductive materials as fluorescent sensors bioimaging. This review summarizes strategies reported synthesis julolidine ring principal modifications obtaining more complex derivatives with improved properties these compounds. In this context, aldol condensation, olefination, imine synthesis, cross‐coupling reactions extensively explored discussed. Examples applications, illustrate structures, will also be briefly presented.

Language: Английский

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Tetrahydroquinolines by the multicomponent Povarov reaction in water: calix[n]arene-catalysed cascade process and mechanistic insights

Organic & Biomolecular Chemistry, Journal Year: 2019, Volume and Issue: 17(11), P. 2913 - 2922

Published: Jan. 1, 2019

The catalyst p-sulfonic acid calix[4]arene was effectively used in the three-component Povarov reaction between aromatic anilines and two equivalents of 2,3-dihydrofuran to obtain furano[3,2-c]-1,2,3,4-tetrahydroquinolines. These reactions proceeded efficiently using water as a green solvent nontoxic catalysts that could be reused; were metal-free only inexpensive easily available compounds. Together with simple workup procedure, these advantages make this protocol very efficient alternative traditional methods for constructing tetrahydroquinoline structures, through formation new C-C bonds one C-N bond. Isotopic labelling experiments revealed mechanism reactions, showing proceeds sequence steps via ionic intermediates, proposed validated.

Language: Английский

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Phosphine-catalyzed [5+1] annulation of β′-acetoxy allenoates: straightforward access to tetrahydroquinoline derivatives

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(78), P. 11712 - 11715

Published: Jan. 1, 2023

An unprecedented phosphine-catalyzed [5+1] annulation of β'-acetoxy allenoates with 1,5-dinucleophiles has been developed, which provides novel and facile access to functionalized tetrahydroquinolines in good high yields the presence PPh3 K3PO4 under mild reaction conditions. Notably, it is first report acting as C1 synthons Lewis base-catalyzed reactions.

Language: Английский

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