Copper(I)-catalysed amidation and successive oxidation of benzylic C(sp3)–H bond: synthesis of 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones

Yan, Xiangqian; Zhang, Zhiguo; Zhang, Guisheng; Ma, Nana; Li, Qingfeng; Liu, Tongxin; Shi, Lei

doi:10.1016/j.tet.2016.05.059

Cited by 16 publications

(6 citation statements)

References 62 publications

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“…The aforementioned catalytic reaction was carried out in the oxone/DMSO based a solvent system and was resistant to a broad range of substrates (See Figure 48). [86] …”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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Copper with variable oxidation states, Earth abundance was used as a tunable and multifunctional catalyst promoting organic transformations. Copper‐based catalytic materials have been effectively utilized in bioorganic chemistry, material science, and natural products synthesis. Several organic transformations involving cycloadditions, cyclizations, cross‐couplings, and condensations in one‐pot assist in the formation of multiple bonds like C−C/C−O bonds, C−C/C−N bonds, and C−N/C−S bonds. Copper has recently been explored as efficient catalytic material for the synthesis of heterocyclic amides. Heterocyclic amides are essential organic compounds are quite prevelent in the pharmaceuticals, fine chemicals and natural products. The heterocyclic amides are the key components of multivarious ace drugs and bio‐molecules like peptides and proteins, and several natural products. Therefore, heterocyclic amides are of much significance, and research focusing on the facile methods is of much interest to contemporary synthetic chemists. Different techniques have been developed using copper‐based catalysts for the synthesis of heterocyclic amdes. These heterocyclic amides are prepared by the reaction of C(sp3)−H, C(sp2)−H, C(sp)−H bonds, aldehydes, ketones, carboxylic acid, carboxylic acid‐based surrogates, and amine surrogates. N‐alkyation of amides with multifarious substrates has been the extensively investigated for the synthesis of heterocyclic amides. Finally, multicomponent domino reactions have also been investigated for the synthesis of heterocycic amides. The present review summarises various synthetic techniques for the copper catalyzed heterocyclic amides synthesis.

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“…The aforementioned catalytic reaction was carried out in the oxone/DMSO based a solvent system and was resistant to a broad range of substrates (See Figure 48). [86] …”

Section: Copper Catalyzed Synthesis Of Heterocyclic Amidesmentioning

confidence: 99%

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Chandra

2021

ChemistrySelect

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“…The R 2 group was then screened during the study. When 4‐chlorophenyl and trifluoromethyl groups were applied for this copper(I)‐catalyzed intramolecular arylmethyl C (sp 3 )‐H direct oxidative amidation reaction, the corresponding fused tricyclic products were created in satisfactory yields under optimized reaction conditions (Scheme ) …”

Section: Design and Synthesis Of Heterocycles Containing Only One Het...mentioning

confidence: 99%

“…When 4-chlorophenyl and trifluoromethyl groups were applied for this copper(I)catalyzed intramolecular arylmethyl C (sp 3 )-H direct oxidative amidation reaction, the corresponding fused tricyclic products were created in satisfactory yields under optimized reaction conditions (Scheme 19). [75] A copper(I)-catalyzed domino transformation for the synthesis of γ-butyrolactone derivatives (71) was presented by Zhu. Using alkenes (69), alkylnitriles (70) and water as the starting substrates, a variety of γbutyrolactone derivatives (71) was successfully and selectively generated in the presence of Cu (BF 4 ) 2 Á6H 2 O as catalyst, Bipy as ligand, DBU as base, Ca (OTf) 2 as Lewis acid and DTBP under a nitrogen atmosphere in acetonitrile at 140 C for 3.5 hr, and afterward 1.0 N hydrochloric acid at 80 C for 45 min.…”

Section: S C H E M E 1mentioning

confidence: 99%

An overview on the copper‐promoted synthesis of five‐membered heterocyclic systems

Shiri

2020

Applied Organom Chemis

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The development of novel approaches for the preparation of small‐sized heterocyclic products has remained an extremely attractive but challenging proposition. Copper has been known as one of the most applicable and significant transition metals utilized in the synthesis of organic products. A couple of factors such as high earth abundance and versatile catalysis resulted in the growth of copper‐promoted synthesis of five‐membered heterocyclic products. Utilizations such as making coins and electrical equipment express the importance of copper, as well. Here, a comprehensive overview of the copper‐catalyzed synthesis of five‐membered heterocyclic products is presented, focusing on the developments over the past 4 years.

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“…Mostly, they are synthesized via multistep reactions, and initiated from the substituted maleimide (Scheme 1a), [8][9] or substituted quinoline precursors (Scheme 1b). [10][11][12] Therefore, the development of effective approaches for the production of pyrroloquinolinediones from readily accessible substrates has become a significant task for synthetic chemists. Adam Daïch, [13] and Imanzadeh, [14] individually reported the three-step synthesis of pyrroloquinolinediones from ortho-carbonyl anilines and dimethyl acetylenedicarboxylate (Scheme 1c).…”

Section: Introductionmentioning

confidence: 99%

PhIO Mediated One‐Pot Synthesis of Pyrroloquinolinediones from ortho‐Carbonyl Anilines and Maleimides

Alahmdi,

Mukhtar,

Parveen

et al. 2024

Eur J Org Chem

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An effective, green, mild, and metal‐free hypervalent iodine‐mediated approach for the synthesis of pyrroloquinolinediones from ortho‐carbonyl anilines and maleimides in a one‐pot manner at room temperature has been developed. This proposed protocol can synthesize biologically active pyrroloquinolinediones in a one‐pot manner utilizing readily available starting materials. This protocol generates H2O as the only by‐product during the reaction and shows a high atom economy. Operational simplicity, moderate reaction conditions, high atom economy, and high yield are some key features of this protocol.

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Copper(I)-catalysed amidation and successive oxidation of benzylic C(sp3)–H bond: synthesis of 1H-pyrrolo[3,4-b]quinoline-1,3(2H)-diones

Cited by 16 publications

References 62 publications

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

Recent Advancement in the Copper Mediated Synthesis of Heterocyclic Amides as Important Pharmaceutical and Agrochemicals

An overview on the copper‐promoted synthesis of five‐membered heterocyclic systems

PhIO Mediated One‐Pot Synthesis of Pyrroloquinolinediones from ortho‐Carbonyl Anilines and Maleimides

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