Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ‐Lactams DOI

Tobias Wagener,

Lukas Lückemeier,

Constantin G. Daniliuc

et al.

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(12), P. 6425 - 6429

Published: Jan. 18, 2021

Abstract Metal‐catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current strategies are limited the formation of C−H and N−H bonds. The stepwise addition hydrogen yields reactive unsaturated intermediates that rapidly reduced. In contrast, interruption complete by further functionalization offers great potential for increasing chemical complexity in a single reaction step. Overcoming tenet full reduction arene has been seldom demonstrated. this work we report synthesis sought‐after, enantioenriched δ‐lactams from oxazolidinone‐substituted pyridines water interrupted mechanism.

Language: Английский

Selective Arene Hydrogenation for Direct Access to Saturated Carbo‐ and Heterocycles DOI Creative Commons
Mario P. Wiesenfeldt, Zackaria Nairoukh, Toryn Dalton

et al.

Angewandte Chemie International Edition, Journal Year: 2019, Volume and Issue: 58(31), P. 10460 - 10476

Published: Jan. 31, 2019

Arene hydrogenation provides direct access to saturated carbo- and heterocycles thus its strategic application may be used shorten synthetic routes. This powerful transformation is widely applied in industry expected facilitate major breakthroughs the sciences. The ability overcome aromaticity while controlling diastereo-, enantio-, chemoselectivity central use of preparation complex molecules. In general, multisubstituted arenes yields predominantly cis isomer. Enantiocontrol imparted by chiral auxiliaries, Brønsted acids, or transition-metal catalysts. Recent studies have demonstrated that highly chemoselective transformations are possible. Such methods underlying strategies reviewed herein, with an emphasis on synthetically useful examples employ readily available

Language: Английский

Citations

249

Piperidine Derivatives: Recent Advances in Synthesis and Pharmacological Applications DOI Open Access
Nikita A. Frolov, A. N. Vereshchagin

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(3), P. 2937 - 2937

Published: Feb. 2, 2023

Piperidines are among the most important synthetic fragments for designing drugs and play a significant role in pharmaceutical industry. Their derivatives present more than twenty classes of pharmaceuticals, as well alkaloids. The current review summarizes recent scientific literature on intra- intermolecular reactions leading to formation various piperidine derivatives: substituted piperidines, spiropiperidines, condensed piperidinones. Moreover, applications natural piperidines were covered, latest advances discovery biological evaluation potential containing moiety. This is designed help both novice researchers taking their first steps this field experienced scientists looking suitable substrates synthesis biologically active piperidines.

Language: Английский

Citations

79

Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines DOI Creative Commons
Marcos Escolano, Daniel Gaviña, G. Alzuet

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(3), P. 1122 - 1246

Published: Jan. 2, 2024

Dearomatization reactions have become fundamental chemical transformations in organic synthesis since they allow for the generation of three-dimensional complexity from two-dimensional precursors, bridging arene feedstocks with alicyclic structures. When those processes are applied to pyridines, quinolines, and isoquinolines, partially or fully saturated nitrogen heterocycles formed, which among most significant structural components pharmaceuticals natural products. The inherent challenge lies low reactivity heteroaromatic substrates, makes dearomatization process thermodynamically unfavorable. Usually, connecting event irreversible formation a strong C–C, C–H, C–heteroatom bond compensates energy required disrupt aromaticity. This aromaticity breakup normally results 1,2- 1,4-functionalization heterocycle. Moreover, combination these subsequent tandem stepwise protocols allows multiple heterocycle functionalizations, giving access complex molecular skeletons. aim this review, covers period 2016 2022, is update state art nucleophilic dearomatizations showing extraordinary ability dearomative methodology indicating their limitations future trends.

Language: Английский

Citations

54

Asymmetric arene hydrogenation: towards sustainability and application DOI Creative Commons

Lukas Lückemeier,

Marco Pierau,

Frank Glorius

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(15), P. 4996 - 5012

Published: Jan. 1, 2023

This review summarises the state-of-the-art in transition-metal catalysed asymmetric hydrogenation of (hetero)arenes and highlights recent advances with a special focus on sustainability while also addressing its shortcomings.

Language: Английский

Citations

53

Synthesis of polysubstituted azepanes by dearomative ring expansion of nitroarenes DOI
Rory C. Mykura, Raquel Sánchez-Bento, Esteban Matador

et al.

Nature Chemistry, Journal Year: 2024, Volume and Issue: 16(5), P. 771 - 779

Published: Jan. 25, 2024

Language: Английский

Citations

39

Chemoselective Heterogeneous Hydrogenation of Sulfur Containing Quinolines under Mild Conditions DOI Creative Commons

Lukas Lückemeier,

Thijs De Vos,

Lisa Schlichter

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(9), P. 5864 - 5871

Published: Feb. 20, 2024

Sulfur, alongside oxygen and nitrogen, holds a prominent position as one of the key heteroatoms in nature medicinal chemistry. Its significance stems from its ability to adopt different oxidation states, rendering it valuable both polarity handle hydrogen bond donor/acceptor. Nevertheless, poisonous free electron pairs makes sulfur containing substrates inaccessible for many catalytic protocols. Strong (at low temperatures) irreversible chemisorption catalyst's surface is particular detrimental heterogeneous catalysts, possessing only few catalytically active sites. Herein, we present novel Ru-S catalyst that tolerates multiple functionalities, including thioethers, thiophenes, sulfoxides, sulfones, sulfonamides, sulfoximines, hydrogenation quinolines. The utility products was further demonstrated by subsequent diversifications functionalities.

Language: Английский

Citations

18

Electrocatalytic reductive deuteration of arenes and heteroarenes DOI

Faxiang Bu,

Yuqi Deng,

Jie Xu

et al.

Nature, Journal Year: 2024, Volume and Issue: 634(8034), P. 592 - 599

Published: Aug. 29, 2024

Language: Английский

Citations

17

Late-Stage Saturation of Drug Molecules DOI Creative Commons

De‐Hai Liu,

Philipp M. Pflüger,

Andrew Outlaw

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(17), P. 11866 - 11875

Published: April 15, 2024

The available methods of chemical synthesis have arguably contributed to the prevalence aromatic rings, such as benzene, toluene, xylene, or pyridine, in modern pharmaceuticals. Many sp

Language: Английский

Citations

16

Direct Dearomatization of Pyridines via an Energy-Transfer-Catalyzed Intramolecular [4+2] Cycloaddition DOI Creative Commons
Jiajia Ma, Felix Strieth‐Kalthoff, Toryn Dalton

et al.

Chem, Journal Year: 2019, Volume and Issue: 5(11), P. 2854 - 2864

Published: Nov. 1, 2019

Language: Английский

Citations

96

A General Catalyst Based on Cobalt Core–Shell Nanoparticles for the Hydrogenation of N‐Heteroarenes Including Pyridines DOI Creative Commons
Kathiravan Murugesan, Vishwas G. Chandrashekhar, Carsten Kreyenschulte

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(40), P. 17408 - 17412

Published: June 16, 2020

Abstract Herein, we report the synthesis of specific silica‐supported Co/Co 3 O 4 core–shell based nanoparticles prepared by template cobalt‐pyromellitic acid on silica and subsequent pyrolysis. The optimal catalyst material allows for general selective hydrogenation pyridines, quinolines, other heteroarenes including acridine, phenanthroline, naphthyridine, quinoxaline, imidazo[1,2‐a]pyridine, indole under comparably mild reaction conditions. In addition, recycling these Co their ability dehydrogenation catalysis are showcased.

Language: Английский

Citations

82