Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C–H Activation/Cyclization of Anilines with Alkynes

Xu, Xuefeng; Yang, Yu‐Rong; Xu, Zhang; Yi, Wei

doi:10.1021/acs.orglett.7b03673

Cited by 86 publications

(33 citation statements)

References 59 publications

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“…For example, various indole and pyrrole derivatives could be easily prepared through Cp*Co(III)‐catalyzed [3+2] cyclization reactions (Scheme , path a) . Moreover, a series of quinolines were synthesized via a Cp*Co(III)‐catalyzed [3+2+1] C−H annulation of anilines with alkynes involving DMSO as the C1 building block (Scheme , path b) . Besides, several groups also achieved the construction of quinoline moieties and quinoline N ‐oxides through the formal [4+2] cyclization reactions (Scheme , path c) .…”

Section: Figurementioning

confidence: 99%

Cobalt(II)‐Catalyzed [5+2] C−H Annulation of o‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[b,d]azepines

et al. 2019

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The first example of CoCl2‐catalyzed formal [5+2] oxidative annulation of o‐arylanilines with alkynes was developed, giving access to various important imine‐containing dibenzo‐[b,d]azepine scaffolds through sequential C−C/C−N bond formation. The reaction employs catalytic amount of manganese and oxygen as cooxidants, and features a broad substrate scope. Preliminary mechanistic studies suggested that C−H activation is involved in the rate‐determining step. Moreover, both internal and terminal alkynes are well tolerated in this transformation. Besides, a regioselective migratory insertion was observed when using terminal alkynes as substrates.

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Section: Figurementioning

confidence: 99%

Cobalt(II)‐Catalyzed [5+2] C−H Annulation of o‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[b,d]azepines

et al. 2019

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“…Recently, Xu et al . (2018) has developed a novel cobalt catalyzed method for the synthesis of quinolines from anilines and alkynes involving DMSO as C1 source via C−H activation and cyclisation strategies (Scheme ) . Herein, K 2 S 2 O 8 is used for the activation of DMSO into active species.…”

Section: Reaction Solvents As Precursors For the Installation Of Key mentioning

confidence: 99%

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

2019

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The solvent is an important entity in a chemical reaction, generally, required for the effective collision of the reactant molecules. By looking at the chemical nature, physic-chemical properties, and more importantly, smart selection, reaction solvents attract synthetic chemists for their effective use as reagents in a chemical reaction. For the installation of small key functionalities in the molecules, reaction solvents provide attractive, atom-economical, greener, and also less costly alternatives to other reagent-based strategies. For instance, particular reaction solvents can serve as a multipurpose building block for various units, such as O,

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“…Xu et al, demonstrated a Co(III)-catalyzed new approach for the synthesis quinolines (226) in which DMSO is involved via C-H activation/coupling of easily accessible anilines (35) with alkynes (225) (Scheme 84). 112 In this reaction, DMSO not only acts as a solvent but also as C 1 building block of the products. The added advantages of this procedure are the enhanced regioselectivity, use of non-toxic solvents and good to excellent yields.…”

Section: Various Approaches For the Synthesis Of Quinolines And Theirmentioning

confidence: 99%

A review on transition-metal mediated synthesis of quinolines

2018

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Quinoline is one of the important class of heterocyclic compounds which have gained considerable importance because of its high pharmaceutical efficacy and broad range of biological activities such as anticancer, anti-malarial, anti-microbial and anti-asthmatic. As a consequence, the desire for new versatile and efficient route for the synthesis of quinoline scaffolds remains an active and growing area of interest both in academia and industry. However, developments of transition-metal catalyzed synthetic methods have witnessed a dominant position over the past few years for the synthesis of diverse range of complex heterocyclics containing quinoline scaffolds. This review specifically provides an overview of the literature available on the transitionmetal catalyzed synthetic methodologies for the synthesis of polysubstituted quinoline derivatives.

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Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C–H Activation/Cyclization of Anilines with Alkynes

Cited by 86 publications

References 59 publications

Cobalt(II)‐Catalyzed [5+2] C−H Annulation of o‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[b,d]azepines

Cobalt(II)‐Catalyzed [5+2] C−H Annulation of o‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[b,d]azepines

Reaction Medium as the Installing Reservoir for Key Functionalities in the Molecules

A review on transition-metal mediated synthesis of quinolines

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