One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(<scp>iii</scp>)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor

Shrestha, Rajeev; Khanal, Hari Datta; Lee, Yong Rok

doi:10.1039/c9ra03146d

Cited by 8 publications

(7 citation statements)

References 36 publications

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“…79−81 In 2019, Rok Lee disclosed a simple and effective Rh(III)-catalyzed annulation of indole 31 with 3-diazoquinolinediones 32 for the construction of various and highly functionalized isochromenoquinolinediones 33 (Scheme 7). 82 The Rh-initiated protocol commenced with the formation of activated [ The developed strategy has the potential to be used to transport a variety of pertinent compounds, including indolopyranoquinolinone, thienopyranoquinolinone, and pyridopyranoquinolindiones. Some of the noteworthy characteristics of this reaction are high atom economy, strong functional group tolerance, and high regioselectivity; the formed substance can also function as a powerful fluorescence sensor for the Fe 3+ ion.…”

Section: Synthesis Of 23-fused Indole Compoundsmentioning

confidence: 99%

“…One of the widely used essential scaffolds in bioactive natural products and medicines is isochromenone or quinonlinone. , They are also regarded as valuable building blocks for synthesizing various pharmaceuticals and useful functional materials. , Additionally, isochromenones with a six-membered lactone ring exhibit potent bioactivity, including anticancer, antibacterial, and anti-HIV properties. − In 2019, Rok Lee disclosed a simple and effective Rh(III)-catalyzed annulation of indole 31 with 3-diazoquinolinediones 32 for the construction of various and highly functionalized isochromenoquinolinediones 33 (Scheme ). The Rh-initiated protocol commenced with the formation of activated [RhCp*(OAc) 2 ] 14 , which then reacted with indole derivative 31 to generate rhodacycle 34 by the loss of acetic acid. The so formed rhodacycle intermediate 34 , then coupled with 32 , with the extrusion of nitrogen gas afforded 35 .…”

Section: Aim and Scope Of Reviewmentioning

confidence: 99%

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[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Singh Chauhan,

Mali,

Dua

et al. 2023

ACS Omega

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Polycyclic fused indoles are ubiquitous in natural products and pharmaceuticals due to their immense structural diversity and biological inference, making them suitable for charting broader chemical space. Indole-based polycycles continue to be fascinating as well as challenging targets for synthetic fabrication because of their characteristic structural frameworks possessing biologically intriguing compounds of both natural and synthetic origin. As a result, an assortment of new chemical processes and catalytic routes has been established to provide unified access to these skeletons in a very efficient and selective manner. Transition-metal-catalyzed processes, in particular from rhodium(III), are widely used in synthetic endeavors to increase molecular complexity efficiently. In recent years, this has resulted in significant progress in reaching molecular scaffolds with enormous biological activity based on core indole skeletons. Additionally, Rh(III)-catalyzed direct C–H functionalization and benzannulation protocols of indole moieties were one of the most alluring synthetic techniques to generate indole-fused polycyclic molecules efficiently. This review sheds light on recent developments toward synthesizing fused indoles by cascade annulation methods using Rh(III)-[RhCp*Cl2]2-catalyzed pathways, which align with the comprehensive and sophisticated developments in the field of Rh(III)-catalyzed indole functionalization. Here, we looked at a few intriguing cascade-based synthetic designs catalyzed by Rh(III) that produced elaborate frameworks inspired by indole bioactivity. The review also strongly emphasizes mechanistic insights for reaching 1–2, 2–3, and 3–4-fused indole systems, focusing on Rh(III)-catalyzed routes. With an emphasis on synthetic efficiency and product diversity, synthetic methods of chosen polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro cages are reviewed. The newly created synthesis concepts or toolkits for accessing diazepine, indol-ones, carbazoles, and benzo-indoles, as well as illustrative privileged synthetic techniques, are included in the featured collection.

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Section: Synthesis Of 23-fused Indole Compoundsmentioning

confidence: 99%

Section: Aim and Scope Of Reviewmentioning

confidence: 99%

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Singh Chauhan,

Mali,

Dua

et al. 2023

ACS Omega

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“…Shrestha et al [44] investigated the construction of various functionalized isoquinolines by the Rh(III)-catalyzed cyclization reaction of 3-protected quinolinediones with unprotected arylamide. Benzamide and 3-diazoquinoline-2,4-dione were used as quinolinedione substrates, and a heterochromatic pyranopyridone structure was generated using [RhCp*Cl 2 ] 2 as catalyst.…”

Section: Scheme 9 Synthetic Route Of Compound 28mentioning

confidence: 99%

Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design

Kong¹,

Yang²,

Zhou³

et al. 2022

Chinese Journal of Organic Chemistry

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Recently, diabetes has gradually become a main life-threatening disease in China. Drug targets for the treatment of diabetes mainly include dipeptidyl peptidase 4 (DPP-4), adenosine monophosphate-activated protein kinase (AMPK), peroxisome proliferator-activated receptor gamma (PPARγ) receptor and so on, in which targeted drug research targeting DPP-4 is a hot spot in recent years. DPP-4 inhibitor is a drug for the treatment of type 2 diabetes, and its biggest advantage is that it is not easy to induce hypoglycemia and increase weight. It is reported that the currently available DPP-4 targeted drugs can cause adverse reactions, such as pancreatitis and hypersensitivity. Therefore, it is worth further studying to continue to develop new hypoglycemic drugs for DPP-4 inhibitors to avoid adverse reactions. According to the systematic literature review, the potential heterocyclic structures with hypoglycemic activity are summarized and through computer molecular simulation docking, five kinds of heterocyclic structures with high hypoglycemic activity and easy synthesis are finally screened out based on DPP-4 target design. The synthesis routes and structure-activity relationships are summarized and analyzed, which provides a research basis for the development of safe, efficient and novel hypoglycemic drugs for DPP-4 inhibitors in the future. Keywords diabetes; dipeptidyl peptidase 4 (DPP-4) inhibitor; molecular docking; synthesis methods; structure-activity relationship

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“…Recently, considerable effort has been realized in the field of directed C–H bond arylation using metal quinoid–carbene species, an umpoled phenol based on the migratory insertion pathway. , However, this strategic pathway mostly relies on expensive transition metal catalysts like Rh or Ir or Pd catalysts. Though Ru–quinoid carbene complexes have been described in the literature, their applications have been limited.…”

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confidence: 99%

Weakly Coordinating tert-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins

Sarkar

Samanta

2022

Org. Lett.

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A weakly coordinating tert-amide-directed straightforward method was developed for the synthesis of azacoumestans using the corresponding azaheterocycle derivatives and diazonaphthoquinones under cheap Ru(II)-catalyzed conditions. The reaction proceeds via migratory insertion of quinoid carbene and subsequent Brønstead acid-mediated cyclization. The optimized C2-selective method offered a wide scope of important azaheterocycles. Bioactive natural products like isolamellarins A and B were synthesized via the developed protocol. Preliminary mechanistic studies highlighted the probable mechanistic pathway.

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One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(iii)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor

Abstract: An efficient Rh(iii)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinedione derivatives is described.

Cited by 8 publications

References 36 publications

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design

Weakly Coordinating tert-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins

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One-pot construction of diverse and functionalized isochromenoquinolinediones by Rh(iii)-catalyzed annulation of unprotected arylamides with 3-diazoquinolinediones and their application for fluorescence sensor

Abstract: An efficient Rh(iii)-catalyzed annulation of arylamides with 3-diazoquinolinediones for the construction of diverse and highly functionalized isochromenoquinolinedione derivatives is described.

Cited by 8 publications

References 36 publications

[RhCp*Cl2]2-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

[RhCp*Cl2]2-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design

Weakly Coordinating tert-Amide-Assisted Ru(II)-Catalyzed Synthesis of Azacoumestans via Migratory Insertion of Quinoid Carbene: Application in the Total Synthesis of Isolamellarins

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[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles