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. 2017 Nov 30;7(1):16640.
doi: 10.1038/s41598-017-16887-0.

A Copper-Catalyzed Tandem Cyclization Reaction of Aminoalkynes with Alkynes for the Construction of Tetrahydropyrrolo[1,2-a]quinolines Scaffold

Can-Liang Ma  1 , Jin-Hao Zhao  2 , Yong Yang  2 , Min-Kui Zhang  1 , Chao Shen  1 , Rong Sheng  3 , Xiao-Wu Dong  4 , Yong-Zhou Hu  5
Affiliations

A Copper-Catalyzed Tandem Cyclization Reaction of Aminoalkynes with Alkynes for the Construction of Tetrahydropyrrolo[1,2-a]quinolines Scaffold

Can-Liang Ma et al. Sci Rep. .

Abstract

A synthetic method for diversely substituted tetrahydropyrrolo[1,2-a]quinolines was developed via CuCl-catalyzed cascade transformation of internal aminoalkynes with alkynes under microwave- irradiation.

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Conflict of interest statement

The authors declare that they have no competing interests.

Figures

Figure 1
Figure 1
Selected biologically active molecules containing the tetrahydropyrrolo[1,2-a]quinoline scaffold.
Figure 2
Figure 2
Synthesis of tetrahydropyrrolo[1,2-a] quinolines.
Figure 3
Figure 3
Screening of reaction conditions.
Figure 4
Figure 4
The scope of aminoalkynes 1. Reaction conditions: 1a (0.1 mmol), 2 (0.3 mmol), catalyst (10 mol %), DMF (3.0 mL), at the corresponding temperature under argon. aIsolated yields are shown.
Figure 5
Figure 5
The scope of alkyne 2. Reaction conditions: 1a (0.1 mmol), 2 (0.3 mmol), catalyst (10 mol %), DMF (3.0 mL), at the corresponding temperature under argon. aIsolated yields are shown.
Figure 6
Figure 6
The reaction of terminal aminoalkyne 1 and alkyne 2a under optimized conditions.
Figure 7
Figure 7
Proposed mechanism for copper-catalyzed tandem cyclization.
Figure 8
Figure 8
LC-HRMS analysis of the reaction mixture of 1b and 2a to identify key intermediate C.
Figure 9
Figure 9
Cell cycle analysis. Cell cycle distribution upon treatment of 3ha varies between capan-2 cell lines. The cell cycle distribution of capan-2 cells was determined by flow cytometry.
See this image and copyright information in PMC

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