A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

Sarkar, Piyali; Sarkar, Sayan; Ghosh, Pradyut

doi:10.3762/bjoc.15.152

Cited by 6 publications

(6 citation statements)

References 50 publications

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“…The final products (16 examples) were obtained in very good to excellent yields, showcasing the efficacy of this recyclable catalyst to promote this reaction in water (Scheme 131G). Under the same reaction conditions, products like the ones depicted in Scheme 131F could also be obtained (3 examples; 85–88 % yield) by replacing the dimedone by the appropriate cyclic diketone [267] …”

Section: Non‐oxindole Derivativesmentioning

confidence: 96%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Section: Non‐oxindole Derivativesmentioning

confidence: 96%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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“…This macrocycle was used to catalyze the multicomponent reaction between isatin 2, dimedone 3 and toluidine 4 to yield the highly substituted pyrroloacridinone 5 (see Figure 1). [16] Little to no conversion was observed in absence of the catalyst, while presence of macrocyclic catalyst 1 (10 mol%) yielded the polycyclic product in up to 91 % yield (see Figure 1). Interestingly, the authors use dispersions of the catalyst in water or water/alcohol mixtures, where catalyst aggregates ranging from 70-100 nm in size were observed.…”

Section: Amine- Amide-or Urea-based Macrocyclic Organocatalystsmentioning

confidence: 98%

“…Gosh and co‐workers described the multifunctional macrocycle 1 consisting of a bisamide and a trisamine unit acting as H‐bond donors. This macrocycle was used to catalyze the multicomponent reaction between isatin 2 , dimedone 3 and toluidine 4 to yield the highly substituted pyrroloacridinone 5 (see Figure ) . Little to no conversion was observed in absence of the catalyst, while presence of macrocyclic catalyst 1 (10 mol%) yielded the polycyclic product in up to 91 % yield (see Figure ).…”

Section: Macrocyclic Organocatalystsmentioning

confidence: 99%

Functionalized Macrocycles in Supramolecular Organocatalysis

Kauerhof

Niemeyer

2020

ChemPlusChem

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Supramolecular organocatalysis has emerged as a novel research field in the context of homogeneous catalysis. In particular, the use of functionalized macrocycles as supramolecular catalysts is highly promising, as these systems are oftentimes easily accessible and offer distinct advantages in catalysis. Macrocyclic catalysts can provide defined binding pockets, such as hydrophobic cavities, and can thus create a reaction microenvironment for catalysis. In addition, macrocycles can offer a preorganized arrangement of functional groups, such as binding sites or catalytically active groups, thus enabling a defined and possibly multivalent binding and activation of substrates. The aim of this Minireview is to provide an overview of recent advances in the area of supramolecular organocatalysis based on functionalized macrocycles (including cyclodextrins, calixarenes, and resorcinarenes), with a focus on those examples where certain catalytically active groups (such as hydrogen bond donors/acceptors, Brønsted acid or base groups, or nucleophilic units) are present in or have been installed on the macrocycles.

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“…[ 14 ] The Heliannuol family comprises substances not only with the same benzofused macrocyclic 8‐membered ether ring system originally proposed for the Helianane family [ 14–18 ] but also with ether rings of five to seven members, all of them with at least two stereogenic centers, as shown in Figure 2. [ 19,20 ] These secondary metabolites present a broad spectrum of biological activities, including the allelochemical activity, making them promising candidates as natural agrochemicals for pest control. [ 14–20 ] It is worth mentioning that, although there is a considerable number of articles describing the total synthesis of Heliannuols, several examples of the class do not present any synthetic proposal.…”

Section: Introductionmentioning

confidence: 99%

“…[ 19,20 ] These secondary metabolites present a broad spectrum of biological activities, including the allelochemical activity, making them promising candidates as natural agrochemicals for pest control. [ 14–20 ] It is worth mentioning that, although there is a considerable number of articles describing the total synthesis of Heliannuols, several examples of the class do not present any synthetic proposal. [ 19 ] In many cases, the proposed structures are based on structural correlations with similar molecules already known in the literature.…”

Section: Introductionmentioning

confidence: 99%

Revisiting the structure of Heliannuol L: A computational approach

Martorano

Brito

Albuquerque

et al. 2021

Magnetic Reson in Chemistry

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Recently, structural elucidation of natural products has undergone a revolution. The combined use of different modern spectroscopic methods has allowed obtaining a complete structural assignment of natural products using small amounts of sample. However, despite the extraordinary ongoing advances in spectroscopy, the mischaracterization of natural products has been and remains a recurrent problem, especially when the substance presents several stereogenic centers. The misinterpretation of nuclear magnetic resonance (NMR) data has resulted in frequent reports addressing structural reassignment. In this context, a great effort has been devoted to developing quantum chemical calculations that simulate NMR parameters accurately, allowing to achieve a more precise spectral interpretation. In this work, we employed a protocol for theoretical calculations of 1H NMR chemical shifts and coupling constants using density functional theory (DFT), followed by the application of the DP4+ method to revisit the structure of Heliannuol L, a member of the Heliannuol class, isolated from Helianthus annuus. Our results indicate that the originally proposed structure of Heliannuol L needs a stereochemical reassignment, placing the hydroxyl bonded to C10 in the opposite side of the methyl and hydroxyl groups bonded to C7 and C8, respectively.

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A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

Cited by 6 publications

References 50 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Functionalized Macrocycles in Supramolecular Organocatalysis

Revisiting the structure of Heliannuol L: A computational approach

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