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

Issa Yavari, Aliyeh Khajeh‐Khezri

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Abstract

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 Introduction 2 Synthesis of Spiro Compounds Employing Acenaphthylene-1,2-dione 2.1 Methods for the Construction of Spiro Compounds 2.1.1 By 1,3-Dipolar Cycloaddition of Acenaphthylene-1,2-dione via Azomethine Ylides 2.1.2 By Multicomponent Reactions of Acenaphthylene-1,2-dione with C–H Acidic Compounds 2.1.3 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates 2.1.4 By Substitution and Multicomponent Reactions of Acenaphth- ylene-1,2-dione with Different Nucleophiles 3 Synthesis of Propellanes by Employing Acenaphthylene-1,2-dione 3.1 Methods for the Construction of Propellanes Based on Acenaph- thylene-1,2-dione 3.1.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles 3.1.2 By Reaction of Acenaphthylene-1,2-dione with Binucleophiles 4 Synthesis of Ligands Employing Acenaphthylene-1,2-dione for Catalyst Reactions 5 Synthesis of Novel Hetero- and Carbocyclic Compounds Employing Acenaphthylene-1,2-dione 5.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles 5.2 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates 5.3 By Ring Opening and Ring Enlargement 6 Conclusion

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What this paper is about

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 Introduction 2 Synthesis of Spiro Compounds Employing Acenaphthylene-1,2-dione 2.1 Methods for the Construction of Spiro Compounds 2.1.1 By 1,3-Dipolar Cycloaddition of Acenaphthylene-1,2-dione via Azomethine Ylides 2.1.2 By Multicomponent Reactions of Acenaphthylene-1,2-dione with C–H Acidic Compounds 2.1.3 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates 2.1.4 By Substitution and Multicomponent Reactions of Acenaphth- ylene-1,2-dione with Different Nucleophiles 3 Synthesis of Propellanes by Employing Acenaphthylene-1,2-dione 3.1 Methods for the Construction of Propellanes Based on Acenaph- thylene-1,2-dione 3.1.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles 3.1.2 By Reaction of Acenaphthylene-1,2-dione with Binucleophiles 4 Synthesis of Ligands Employing Acenaphthylene-1,2-dione for Catalyst Reactions 5 Synthesis of Novel Hetero- and Carbocyclic Compounds Employing Acenaphthylene-1,2-dione 5.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles 5.2 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates 5.3 By Ring Opening and Ring Enlargement 6 Conclusion

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Available abstract

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 Introduction 2 Synthesis of Spiro Compounds Employing Acenaphthylene-1,2-dione 2.1 Methods for the Construction of Spiro Compounds 2.1.1 By 1,3-Dipolar Cycloaddition of Acenaphthylene-1,2-dione via Azomethine Ylides 2.1.2 By Multicomponent Reactions of Acenaphthylene-1,2-dione with C–H Acidic Compounds 2.1.3 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates 2.1.4 By Substitution and Multicomponent Reactions of Acenaphth- ylene-1,2-dione with Different Nucleophiles 3 Synthesis of Propellanes by Employing Acenaphthylene-1,2-dione 3.1 Methods for the Construction of Propellanes Based on Acenaph- thylene-1,2-dione 3.1.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles 3.1.2 By Reaction of Acenaphthylene-1,2-dione with Binucleophiles 4 Synthesis of Ligands Employing Acenaphthylene-1,2-dione for Catalyst Reactions 5 Synthesis of Novel Hetero- and Carbocyclic Compounds Employing Acenaphthylene-1,2-dione 5.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles 5.2 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates 5.3 By Ring Opening and Ring Enlargement 6 Conclusion

Key concepts: Acenaphthylene, Nucleophile, Chemistry, Medicinal chemistry, Cycloaddition, Catalysis, Organic chemistry, Naphthalene

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