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Synlett 2019; 30(19): 2148-2152
DOI: 10.1055/s-0039-1690724
DOI: 10.1055/s-0039-1690724
letter
Acetic Acid Catalysed One-Pot Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives
We thank London Metropolitan University for funding.
Further Information
Publication History
Received: 11 September 2019
Accepted after revision: 07 October 2019
Publication Date:
22 October 2019 (online)
Abstract
An efficient acetic acid catalysed reaction has been developed for the synthesis of 4-aryl substituted pyrrolo[1,2-a]quinoxalines from readily available starting materials. A range of structures have been synthesised in very good to excellent yields. The one-pot reaction proceeds through imine formation, cyclisation followed by air oxidation.
Key words
pyrrolo[1,2-a]quinoxaline - catalysis - Pictet–Spengler reaction - 1-(2-aminophenyl)pyrroles - biological heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690724.
- Supporting Information
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- 22 Typical Procedure for the Synthesis of Pyrrolo[1,2-a]quinoxaline 3a: To a solution of 2-(1H-pyrrol-1-yl)aniline (1 equiv) in methanol (5 mL) were added benzaldehyde (1 equiv) and acetic acid (0.1 equiv) and the mixture was heated to 60 °C for 8 h. The reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The crude reaction mixture was purified by column chromatography to give 2-substituted pyrrolo[1,2-a]quinoxaline 3a as a pale-yellow solid; mp 118–120 °C. IR (neat): 2929 (CH) cm–1. 1H NMR (500 MHz, CDCl3): δ = 8.07 (dd, J = 7.7, 1.4 Hz, 1 H, ArH), 7.99–8.04 (m, 5 H, 5 × ArH), 7.88 (dd, J = 8.0, 1.4 Hz, 1 H, ArH), 7.01 (dd, J = 3.8, 1.3 Hz, 1 H, ArH), 6.90 (dd, J = 3.9, 2.7 Hz, 1 H, ArH). 13C (126 MHz, CDCl3): δ = 154.4 (C), 138.4 (C), 136.2 (C), 130.2 (CH), 129.7 (CH), 128.6 (2 × CH), 128.5 (2 × CH), 127.4 (CH), 127.1 (C), 125.3 (C), 125.2 (CH), 114.5 (CH), 113.9 (CH), 113.6 (CH), 108.7 (CH). MS: m/z (%) = 244 (100) [M + H]+.
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