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Synlett 2020; 31(04): 359-362
DOI: 10.1055/s-0037-1610743
DOI: 10.1055/s-0037-1610743
letter
Copper-Catalyzed Synthesis of Alkyl-Substituted Pyrrolo[1,2-a]quinoxalines from 2-(1H-Pyrrol-1-yl)anilines and Alkylboronic Acids
This work was supported by the National Natural Science Foundation of China (21672086) and by the Fundamental Research Funds for the Central Universities (lzujbky-2018-81).Further Information
Publication History
Received: 03 December 2019
Accepted after revision: 02 January 2020
Publication Date:
17 January 2020 (online)
Abstract
A radical pathway for the construction of pyrrolo[1,2-a]quinoxalines by using 2-(1H-pyrrol-1-yl)anilines and alkylboronic acids has been developed. Features of this process include Cu catalysis, readily accessible starting materials, and simple operations. Alkylboronic acids are used for the construction of pyrrolo[1,2-a]quinoxaline derivatives, and the desired products are obtained in moderate yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610743.
- Supporting Information
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- 16 4-Propylpyrrolo[1,2-a]quinoxaline (3aa):2 Typical Procedure A mixture of 2-(1H-pyrrol-1-yl)aniline (1a; 1 equiv, 0.3 mmol), BuB(OH)2 (2a; 3 equiv, 0.9 mmol), PivOH (1 equiv, 0.3 mmol), Cu(OPiv)2 (10 mol%, 0.03 mmol), and DCM (1 mL) was stirred at 80 °C under O2 (balloon) for 8 h. Upon completion of the reaction (TLC), the mixture was concentrated in vacuo, and the crude product was purified by column chromatography [silica, gel, PE–EtOAc (10:1)] to give a light-yellow solid; yield: (40.3 mg, 73%); mp 45–46 °C. 1H NMR (400 MHz, CDCl3): δ = 7.94–7.90 (m, 1 H), 7.90–7.89 (m, 1 H), 7.84–7.80 (m, 1 H), 7.49–7.44 (m, 1 H), 7.44–7.39 (m, 1 H), 6.92–6.89 (m, 1 H), 6.85–6.83 (m, 1 H), 3.02–2.97 (m, 2 H), 1.99–1.89 (m, 2 H), 1.10–1.05 (m, 3 H). 13C NMR (100 MHz, CDCl3): δ = 157.4, 136.0, 129.4, 127.3, 126.8, 126.1, 125.0, 114.1, 113.6, 113.4, 106.3, 37.8, 22.0, 14.3. HRMS (ESI): m/z [M + H]+ calcd for C14H15N2: 211.1230; found: 211.1227.