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Synthesis 2018; 50(20): 3947-3973
DOI: 10.1055/s-0037-1610209
review
© Georg Thieme Verlag Stuttgart · New York

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

Issa Yavari*
Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran   Email: yavarisa@modares.ac.ir
,
Aliyeh Khajeh-Khezri
› Author Affiliations
Further Information

Publication History

Received: 23 April 2018

Accepted after revision: 12 June 2018

Publication Date:
16 August 2018 (online)

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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

Key words

acenaphthylene-1,2-dione - 1,3-dipolar cycloaddition - heterocycles­ - spiro compounds - propellanes