Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds

Lin, Yu Chuan; Fu, Zhijie; Shen, Tianhua; Che, Fengfeng; Song, Qingbao

doi:10.1080/00397911.2015.1066390

Cited by 8 publications

(3 citation statements)

References 9 publications

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“…The regioselectivity of these reactions has been explained by analysis of the activation barriers and global and local reactive indices by DFT calculations. Song et al 28 reported the regioselective synthesis of spiro[acenaphthylene-1,2′-pyrrolidin]-2-one derivatives 67 in 67-93% yields via [3+2] cycloaddition reactions. The azomethine ylide, generated in situ by condensation of 1 with arylmethyl amines 68, undergoes cycloaddition with the conjugated double bond of the chalcone derivative 7 to afford the corresponding spirocycloadducts in a regio-and stereocontrolled manner (Scheme 22).…”

Section: Scheme 20 13-dipolar Cycloaddition Reaction Of Curcumin (63mentioning

confidence: 99%

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

Yavari

Khajeh-Khezri²

2018

Synthesis

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Acenaphthylene-1,2-dione has been utilized in a wide range of reactions as a starting material for the synthesis of hetero- and carbocyclic compounds and complexes. This review provides a short summary of the recent advances in the application of acenaphthylene-1,2-dione in the synthesis of hetero- and carbocyclic systems and bioactive compounds. In addition, the applications of acenaphthylene-1,2-dione in the synthesis of spiro compounds, propellanes, and ligands in catalyst reactions, from 2002 to early 2018, are included.1 Introduction2 Synthesis of Spiro Compounds Employing Acenaphthylene-1,2-dione2.1 Methods for the Construction of Spiro Compounds2.1.1 By 1,3-Dipolar Cycloaddition of Acenaphthylene-1,2-dione via Azomethine Ylides2.1.2 By Multicomponent Reactions of Acenaphthylene-1,2-dione with C–H Acidic Compounds2.1.3 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates2.1.4 By Substitution and Multicomponent Reactions of Acenaphth- ylene-1,2-dione with Different Nucleophiles3 Synthesis of Propellanes by Employing Acenaphthylene-1,2-dione3.1 Methods for the Construction of Propellanes Based on Acenaph- thylene-1,2-dione3.1.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles3.1.2 By Reaction of Acenaphthylene-1,2-dione with Binucleophiles4 Synthesis of Ligands Employing Acenaphthylene-1,2-dione for Catalyst Reactions5 Synthesis of Novel Hetero- and Carbocyclic Compounds Employing Acenaphthylene-1,2-dione5.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles5.2 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates5.3 By Ring Opening and Ring Enlargement6 Conclusion

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Section: Scheme 20 13-dipolar Cycloaddition Reaction Of Curcumin (63mentioning

confidence: 99%

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

Yavari

Khajeh-Khezri²

2018

Synthesis

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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)…”

mentioning

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…”

mentioning

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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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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Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

et al. 2021

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The synthesis of 1-pyrrolines from N-alkenylnitrones and alkynes has been explored as ar etrosynthetic alternative to traditional approaches.T hese cascade reactions are formal [4 + 1] cycloadditions that proceed through ap roposed dipolar cycloaddition and N-alkenylisoxazoline [3,3']sigmatropic rearrangement. Av ariety of cyclic alkynes and terminal alkynes have been shown to undergo the transformation with N-alkenylnitrones under mild conditions to provide the corresponding spirocyclic and densely substituted 1-pyrrolines with high regio-and diastereoselectivity.M echanistic studies provide insight into the balance of steric and electronic effects that promote the cascade process and control the diastereo-and regioisomeric preferences of the 1-pyrroline products.D iastereoselective derivatization of the 1-pyrrolines prepared by the cascade reaction demonstrate the divergent synthetic utility of the new method.Scheme 1. N-Alkenylisoxazoline approach to 1-pyrroline synthesis.LG = leaving group. EWG = electron-withdrawing group.

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Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds

Cited by 8 publications

References 9 publications

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

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

Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

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Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds

Cited by 8 publications

References 9 publications

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione

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

Nitrone and Alkyne Cascade Reactions for Regio‐ and Diastereoselective 1‐Pyrroline Synthesis

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Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione