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Synthesis 2020; 52(24): 3818-3836
DOI: 10.1055/s-0040-1707355
special topic
Recent Advances in Metal-Catalyzed Ring Construction

Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles

Jing-Hao Qin
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China   Email: deliean@hnu.edu.cn   Email: jhli@hnu.edu.cn
,
Jin-Heng Li∗
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China   Email: deliean@hnu.edu.cn   Email: jhli@hnu.edu.cn
b   Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, P. R. of China
c   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
,
De-Lie An∗
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China   Email: deliean@hnu.edu.cn   Email: jhli@hnu.edu.cn
› Author AffiliationsThis research was supported by the National Natural Science Foundation of China (Nos. 21625203 and 21871126).
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Abstract

Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.

1 Introduction

2 Intermolecular Cycloaddition To Construct Azepine Derivatives

2.1 [5+2] Cycloaddition

2.2 [3+2+2] Cycloaddition

2.3 [3+2]/[5+2] Cycloaddition

3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins

4 Intermolecular [3+2] Cycloaddition To Construct Spirohetero­cyclic Compounds, Indoles, Furans, and Pyrroles

5 Summary and Outlook

Key words

cycloaddition - transition metals - alkynes - heterocycles - tandem reaction


Publication History

Received: 30 April 2020

Accepted: 24 July 2020

Article published online:
13 October 2020

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