Synthesis of Succinimide-Containing Chromones, Naphthoquinones, and Xanthones under Rh(III) Catalysis: Evaluation of Anticancer Activity

Han, Sang Hoon; Kim, Saegun; De, Umasankar; Mishra, Neeraj Kumar; Park, Ji-Hye; Sharma, Satyasheel; Kwak, Jong Hwan; Han, Sim-Hee; Kim, Hyung Sik; Kim, In Su

doi:10.1021/acs.joc.6b02577

Cited by 88 publications

(29 citation statements)

References 45 publications

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“…One year later, Kim and Kim reported a similar protocol applied to chromones and xanthones. 84 By switching to a Rh catalyst, they could reduce the catalyst loading significantly ( Scheme 2B ). Acetyl-directed alkylation (as well as amidation and alkenylation) was also reported by Zhang ( Scheme 2C ).…”

Section: Ketone Dgsmentioning

confidence: 99%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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Section: Ketone Dgsmentioning

confidence: 99%

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

et al. 2018

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“…In 2016, Kim's group reported a rhodium(III)‐catalyzed C−H alkylation of weakly directing chromone derivatives . When 4 H ‐chromen‐4‐one ( 31 a ) was treated with N ‐methyl maleimide ( 7 a ) in the presence of [Cp*RhCl 2 ] 2 (2.5 mol%), AgSbF 6 (10 mol%) and PivOH (100 mol%) at 80 °C in DCE for 20 h, an ortho alkylated chromone derivative 32 a was observed in 95% yield (Scheme ).…”

Section: Ortho Alkylation Of Aromatics With Maleimidesmentioning

confidence: 99%

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

2019

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Maleimide and succinimide core moieties are present in various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines and γ-lactams. A transition-metal-catalyzed chelationassisted functionalization of inert CÀ H bond of organic molecules with electrophiles or nucleophiles is one of the efficient methods to construct chemical bonds in a highly atom-and step-economical manner. The present review describes the recent advances in the reaction involving maleimides with organic molecules by a chelation-assisted inert CÀ H bond activation methodology. The reaction involving maleimides with organic molecules having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N-sulfonyl ketimine, carboxylic acids, and aldimines, were described. The scope, limitation and mechanistic investigation of the alkylation, annulation and alkenylation reactions were discussed elaborately. This review article includes the entire report on the chemical bondforming reaction of maleimides with organic molecules by the CÀ H bond activation strategy until the end of 2018.

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“…Some of these succinimide derivatives represent important intermediates in the synthesis of drugs [17,18] and other organic compounds [19,20]. Chromones, naphthoquinones, and xanthones bearing succinimide are shown to be highly cytotoxic comparable to activity of the anticancer agent doxorubicin [21]. Besides their significant biological role, they are, also, used as dopants necessary for generation of blue phases, which are considered to be the next-generation of fast liquid crystals displays [22], as well as an efficient and recyclable catalyst in form of succinimide sulfonic acid [23].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potentional anticonvulsant agents

Cvetković¹,

Božić

Banjac³

et al. 2019

Hem Ind

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Novel succinimide derivatives were synthesized from 3-methyl-3-phenylsuccinic acid and substituted anilines under solvent-free conditions by using microwave irradiation. All obtained compounds were characterized by ultraviolet (UV), Fourier-transform infrared (FT-IR), 1 H and 13 С nuclear magnetic resonance (NMR) spectroscopy as well as by elemental analysis. The influence of the substituent electronic effects on spectroscopic data was analyzed by applying the Hammett equation. Moreover, a detailed interpretation and comparison of experimentally obtained and theoretically calculated FT-IR, UV and NMR spectra was performed. Density functional theory (DFT) calculated data of the investigated succinimides were obtained and analyzed in order to determine their structural, spectroscopic and electronic properties. Furthermore, ADMET factor profiling and in-silico prediction of potential biological activities of novel succinimide derivatives have been performed.

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Synthesis of Succinimide-Containing Chromones, Naphthoquinones, and Xanthones under Rh(III) Catalysis: Evaluation of Anticancer Activity

Cited by 88 publications

References 45 publications

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation

Spectroscopic and quantum chemical elucidation of newly synthesized 1-aryl-3-methyl-3-phenylpyrrolidine-2,5-diones as potentional anticonvulsant agents

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