One-Pot Tandem Nickel-Catalyzed α-Vinyl Aldol Reaction and Cycloaddition Approach to [1,2,3]Triazolo[1,5-<i>a</i>]quinolines

Borra, Satheesh; Kim, Hun Young; Oh, Kyungsoo

doi:10.1021/acs.orglett.2c04188

Cited by 5 publications

(3 citation statements)

References 48 publications

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“…[213] In a different work, α-allenones prepared in situ from chlorovinyl ketones 465 have generated [1,2,3]triazolo [1,5-a]quinolines 467 from the reaction with 2-azidoaryl carbonyls 466 under Ni catalysis (Scheme 79b). [214] Keto-vinylidenecyclopropanes 119 a have been devised as precursors of cyclic aminoalcohols 470 through a transition metal catalyzed annulation process involving the allenone moiety (Scheme 80a). [215] An initial rhodium-catalyzed oxidative addition to allenic systems 119 a with concomitant ring opening of the cyclopropane nucleus has resulted in complexes 471, which is followed by a carbometallation process providing the piperidine ring in intermediates 472.…”

Section: Synthesis Of Nitrogen Heterocyclesmentioning

confidence: 99%

“…Iridium catalyst 464 has provided substrate controlled enantioselectivity of up to 99% through a hydrogen borrowing catalytic reaction mechanism (Scheme 79a) [213] . In a different work, α‐allenones prepared in situ from chlorovinyl ketones 465 have generated [1,2,3]triazolo[1,5‐ a ]quinolines 467 from the reaction with 2‐azidoaryl carbonyls 466 under Ni catalysis (Scheme 79b) [214] …”

Section: Synthetic Utilitymentioning

confidence: 99%

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Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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Conjugated and non-conjugated allenones appear as recurring motifs in organic synthesis, natural products and mechanistic investigations showing unique properties and applications. The ability of allenones to build cycles has provided a direct access to strained systems, medium-sized rings, arenes, heterocycles and complex polycycles. In addition, allenones have served as models in mechanistic investigations and catalysis. The critic compilation herein presented will provide an exhaustive overview of the synthetic possibilities allenones may offer, which certainly will inspire our community in their search of more efficient synthetic methodologies, preparation of biological and pharmaceutical targets, and improve our knowledge in theoretical organic chemistry. Great part of this review will discuss synthetic aspects, catalysis innovation and mechanistic insights of the chemical transformations implying the allenone motif. In addition, many examples on total synthesis and pharmacologically active compounds will be described. We hope that this overview will be attractive to the organic chemistry, synthetic chemistry, catalysis, theoretical chemistry, natural products and medicinal chemistry communities. 3.5. Synthesis of Spirocycles and Bridged Structures 3.6. Open-Chain Structures from Allenones 3.7. Allenones in Total Synthesis 4.

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Section: Synthesis Of Nitrogen Heterocyclesmentioning

confidence: 99%

Section: Synthetic Utilitymentioning

confidence: 99%

Highlighting the Rich Chemistry of the Allenone Moiety

Almendros

Alonso

2023

Adv Synth Catal

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“…Various antimicrobial triazole derivatives have Molecules 2023, 28, 7876 2 of 16 been developed and most of them show potent antimicrobial activity [8]. It is particularly noteworthy that more effective antibacterial candidates might be obtained from the various triazole fused heterocyclic derivatives, extensively existing in chemistry, such as triazolo[1,5-a]pyrimidine [9], triazolo [4,5-c]pyridine [10], triazolo [4,3-a]pyrazine [11], triazolo [4,5-d]pyrimidine [12], triazolo [4,3-a]quinoxaline [13], triazolo[1,5-a]quinolines [14], and triazolo[1,5-a]pyridine [15,16]. Some triazole fused heterocyclic derivatives have been found to have high antibacterial activity against both drug-sensitive and drug-resistant pathogens and are not inferior to the first-line antimicrobial agents [17,18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Hu,

Dong,

et al. 2023

Molecules

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Infectious diseases pose a major challenge to human health, and there is an urgent need to develop new antimicrobial agents with excellent antibacterial activity. A series of novel triazolo[4,3-a]pyrazine derivatives were synthesized and their structures were characterized using various techniques, such as melting point, 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis. All the synthesized compounds were evaluated for in vitro antibacterial activity using the microbroth dilution method. Among all the tested compounds, some showed moderate to good antibacterial activities against both Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli strains. In particular, compound 2e exhibited superior antibacterial activities (MICs: 32 μg/mL against Staphylococcus aureus and 16 μg/mL against Escherichia coli), which was comparable to the first-line antibacterial agent ampicillin. In addition, the structure–activity relationship of the triazolo[4,3-a]pyrazine derivatives was preliminarily investigated.

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Comprehensive Review on the Synthesis of [1,2,3]Triazolo[1,5‐a]Quinolines

Da Costa,

Sacramento,

Barcellos

et al. 2024

The Chemical Record

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This report outlines the evolution and recent progress about the different protocols to synthesize the N‐heterocycles fused hybrids, specifically [1,2,3]triazolo[1,5‐a]quinoline. This review encompasses a broad range of approaches, describing several reactions for obtaining this since, such as dehydrogenative cyclization, oxidative N−N coupling, Dieckmann condensation, intramolecular Heck, (3+2)‐cycloaddition, Ullman‐type coupling and direct intramolecular arylation reactions. We divided this review in three section based in the starting materials to synthesize the target [1,2,3]triazolo[1,5‐a]quinolines. Starting materials containing quinoline or triazole units previously formed, as well as starting materials which both quinoline and triazole units are formed in situ. Different methods of obtaining are described, such as metal‐free or catalyzed conditions, azide‐free, using conventional heating or alternative energy sources, such as electrochemical and photochemical methods. Mechanistic insights underlying the reported reactions were also described in this comprehensive review.

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One-Pot Tandem Nickel-Catalyzed α-Vinyl Aldol Reaction and Cycloaddition Approach to [1,2,3]Triazolo[1,5-a]quinolines

Cited by 5 publications

References 48 publications

Highlighting the Rich Chemistry of the Allenone Moiety

Highlighting the Rich Chemistry of the Allenone Moiety

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Comprehensive Review on the Synthesis of [1,2,3]Triazolo[1,5‐a]Quinolines

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