Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

Wang, Qian; Osipyan, Angelina; Konstantinidou, Markella; Butera, Roberto; Mgimpatsang, Kumchok C; Shishkina, Svitlana V.; Dömling, Alexander

doi:10.1021/acs.joc.9b01258

Cited by 16 publications

(9 citation statements)

References 25 publications

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“…Exploring remarkable synthetic strategies for the facile construction of highly functionalized molecules under simple and mild reaction conditions, are strongly demanded and continue to attract the attention of the synthetic community [10–11] . Contrary to the classical organic reactions, isocyanide‐based multicomponent reactions (IMCRs) are such well recognized approach which easily, fast and efficiently combine three or more reactants to afford an adduct with minimum loss of atoms in just one assembly step [12] .…”

Section: Figurementioning

confidence: 99%

Regioselective Synthesis of 2,3‐Dihydrobenzo[f]isoindolones via Ag‐Catalyzed Sequential Ugi 4CR/Cascade Radical Cyclization Reaction

Yan

Ren

et al. 2021

Adv Synth Catal

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An approach to 2,3‐dihydrobenzo[f]isoindolones by a Ag‐catalyzed Ugi 4CR/cascade radical cyclization sequence under mild conditions has been developed. The reaction of (E)‐2‐benzylidene‐4‐arylbut‐3‐ynoic acids, aldehydes, amines, and isocyanides produced 2,3‐dihydro‐benzo[f]isoindolones regioselectively in 60–85% yields via sequential Ugi 4CR/cascade radical cyclization reaction in the presence of Cs2CO3 and AgOTf. The method achieved the formation of two C−C bonds under air atmosphere in one‐pot fashion.

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Section: Figurementioning

confidence: 99%

Regioselective Synthesis of 2,3‐Dihydrobenzo[f]isoindolones via Ag‐Catalyzed Sequential Ugi 4CR/Cascade Radical Cyclization Reaction

Yan

Ren

et al. 2021

Adv Synth Catal

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“…The most recent example of the Ugi reaction was presented by Dömling and coworkers [ 137 ]. Indole-2-carboxylic acids 164 can be used as a platform for the preparation of the tetracyclic scaffolds 166 .…”

Section: Miscellaneousmentioning

confidence: 99%

“…In their work, a similar 6-endo-dig hydroarylation was designed by employing cationic Pd-catalysts to furnish 2-quinolones. The most recent example of the Ugi reaction was presented by Dömling and coworkers [137]. Indole-2-carboxylic acids 164 can be used as a platform for the preparation of the tetracyclic scaffolds 166.…”

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confidence: 99%

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Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

2020

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It is known that 2-quinolones are broadly applicable chemical structures in medicinal and agrochemical research as well as various functional materials. A number of current publications about their synthesis and their applications emphasize the importance of these small molecules. The early synthetic chemistry originated from the same principle of the classical Friedländer and Knorr procedures for the preparation of quinolines. The analogous processes were developed by applying new synthetic tools such as novel catalysts, the microwave irradiation method, etc., whereas recent innovations in new bond forming reactions have allowed for novel strategies to construct the core structures of 2-quinolones beyond the bond disconnections based on two classical reactions. Over the last few decades, some reviews on structure-based, catalyst-based, and bioactivity-based studies have been released. In this focused review, we extensively surveyed recent examples of one-pot reactions, particularly in view of modular approaches. Thus, the contents are categorized as three major sections (two-, three-, and four-component reactions) according to the number of reagents that ultimately compose atoms of the core structures of 2-quinolones. The collected synthetic methods are discussed from the perspectives of strategy, efficiency, selectivity, and reaction mechanism.

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“… 8 It has attracted much attention due to the possibility of introducing versatile functional groups in the Ugi adducts, which can undergo further condensations or cyclization reactions, leading to an array of structurally diverse scaffolds. 9 Specifically, the Ugi four-component reaction (Ugi-4-CR) utilizing ammonia as the amine component can be an extremely valuable approach because it is inexpensive, is easily available, and permits reduced waste. However, relatively fewer studies have focused on it, most of which report an excessive byproduct formation and low yield ( Figure 1 B–D).…”

Section: Introductionmentioning

confidence: 99%

Copper-Catalyzed Modular Assembly of Polyheterocycles

et al. 2020

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Easy operation, readily accessible starting materials, and short syntheses of the privileged scaffold indeno[1,2- c ]isoquinolinone were achieved by an multicomponent reaction (MCR)-based protocol via an ammonia–Ugi-four component reaction (4CR)/copper-catalyzed annulation sequence. The optimization and scope and limitations of this short and general sequence are described. The methodology allows an efficient construction of a wide variety of indenoisoquinolinones in just two steps.

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Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles

Cited by 16 publications

References 25 publications

Regioselective Synthesis of 2,3‐Dihydrobenzo[f]isoindolones via Ag‐Catalyzed Sequential Ugi 4CR/Cascade Radical Cyclization Reaction

Regioselective Synthesis of 2,3‐Dihydrobenzo[f]isoindolones via Ag‐Catalyzed Sequential Ugi 4CR/Cascade Radical Cyclization Reaction

Recent Advances in One-Pot Modular Synthesis of 2-Quinolones

Copper-Catalyzed Modular Assembly of Polyheterocycles

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