Synthesis of 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione derivatives via a one-pot, three-component reaction under catalyst-free conditions

Che, Fengfeng; Wang, Yongsheng; Shen, Tianhua; An, Xiaoxia; Song, Qingbao

doi:10.1016/j.crci.2014.09.013

Cited by 7 publications

(3 citation statements)

References 17 publications

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“…It is notable to mention here that after completion of the reaction, tautomerisation occurred in the pyrazolone rings of 5, which may exist in two tautomeric forms. Based on the X-ray crystal structure analyses in our previous work [18][19][20][21][22][23][24][25] and Tu's work 26 , it could be concluded that the desired products have two different structures: C=O form structure (Table 2, entries 5aa-5dc)…”

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confidence: 97%

“…[11][12][13][14][15][16][17] It is promising that the integration of these two bioactive units into a single molecule may exhibit new or improved pharmacological properties.Considering the above points, and also in continuation of our interest on the synthesis of different kinds of heterocyclic compounds based on MCRs. [18][19][20][21][22][23][24][25] Herein we wish to report MgCl 2 as a low-toxic catalyst for one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione…”

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confidence: 99%

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MgCl2 catalyzed one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives in EG

Qian

et al. 2016

Tetrahedron Letters

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In the past decades, Multi-component reactions (MCRs) have been shown to be powerful tools for the synthesis of biologically active compounds and drug candidates from simple and readily accessible starting materials. 1 They offer significant advantages over conventional synthetic strategies by shortening reaction time, reducing waste, saving energy and making full use of starting materials. [2][3][4] Furthermore, the design of MCRs for the development of efficient chemical syntheses of complex and high added value molecules is another attractive area in chemistry. [5][6][7] Naphthoquinone derivatives particularly 3-substituted-2-hydroxy-1,4-naphthoquinones are of much importance because this fragment is a key moiety in numerous biologically active compounds. 8 For example as showed in the figure 1, atovaquone, lapachol, parvaquone and buparvaquone (Figure 1, first row) exhibit antimalarial, antibacterial, antiprotozoal, antitumor activities. 9 Similarly, pyrazolone framework is a well-known heterocycle in many drug substances of medicinal fields. To list some pyrazolone derivatives ( figure 1, seond row) such as antipyrine (phenazone), 4-aminopyrine (aminophenazone), metamizol (novalgin), and 4-isopropylpyrine (propyphenazone) are all useful antipyretic and analgesic drugs. 10 Pyrazolone derivatives also have ubiquitous applications in the development of acaricides, dyes, fungicides, herbicides, insecticides, inhibitors and reagents. [11][12][13][14][15][16][17] It is promising that the integration of these two bioactive units into a single molecule may exhibit new or improved pharmacological properties.Considering the above points, and also in continuation of our interest on the synthesis of different kinds of heterocyclic compounds based on MCRs. [18][19][20][21][22][23][24][25] Herein we wish to report MgCl 2 as a low-toxic catalyst for one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione

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confidence: 97%

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confidence: 99%

MgCl2 catalyzed one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives in EG

Qian

et al. 2016

Tetrahedron Letters

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“…As part of our ongoing efforts to explore environmentallyfriendly protocols for the construction of biologically important heterocyclic ring systems, [18][19][20][21] we now report for the first time, a one-pot three-component reaction which affords a series of novel spiro[indoline-3,7′-pyrrolo [1,2-c]imidazole] derivatives catalysed by NaHCO 3 in water. All the compounds were evaluated for CDC25B inhibitory activity subsequently.…”

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confidence: 99%

A Green, Facile Approach for the Multicomponent Synthesis of Bioactive Spiro[Indoline-3,7′-Pyrrolo[1,2-c]Imidazole] Derivatives

Shen

Zhou

Che

et al. 2015

Journal of Chemical Research

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Progress in the Synthesis of Oxindole‐Naphthoquinone Molecular Hybrid Scaffolds: A Concise Review

et al. 2020

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Oxindole and 1,4-Naphthoquinone both are the versatile heterocyclic scaffolds which not only found in many naturally occurring and pharmaceutically imperative compounds but also have explored as an important precursor in the synthesis of a library of structurally diverse molecular frameworks desirable for biological studies. For a few decades, significant emphasis is given on the synthesis of both of these important privileged scaffolds to accomplish promising new heterocycles with chemical and biomedical relevance. Due to such prevalence and prominence of oxindole and 1,4-naphthoquinone frameworks in medicinal and synthetic chemistry, many researchers have taken efforts to synthesize the oxindolenaphthoquinone molecular hybrid in a single nucleolus. These efforts have led to the development of different approaches and green technologies in recent years, which includes nano catalysts, microwaves and, ultrasound irradiation. In this review, we have focused our attention, specifically, to provide insight into the modern approaches to the synthesis of oxindole-1,4naphthoquinone molecular hybrid and technical advances in this research field till April 2020. The review is mainly made up of four main parts which contain 2-component, 3-component, 4-component, and other multistep miscellaneous approaches utilized to synthesize this oxindole-1,4-naphthoquinone molecular hybrid. These four main parts are also subdivided according to different substituents present on oxindole-1,4naphthoquinone molecular hybrid. This review focused specifically on the collection of literature on the reaction of isatin with 2-hydroxyl-1,4-naphthoquinone(Lawsone) to afford oxindole-1,4-naphthoquinone molecular hybrid.

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Synthesis of 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxynaphthalene-1,4-dione derivatives via a one-pot, three-component reaction under catalyst-free conditions

Cited by 7 publications

References 17 publications

MgCl2 catalyzed one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives in EG

MgCl2 catalyzed one-pot synthesis of 2-hydroxy-3-((5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)naphthalene-1,4-dione derivatives in EG

A Green, Facile Approach for the Multicomponent Synthesis of Bioactive Spiro[Indoline-3,7′-Pyrrolo[1,2-c]Imidazole] Derivatives

Progress in the Synthesis of Oxindole‐Naphthoquinone Molecular Hybrid Scaffolds: A Concise Review

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