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Synlett 2022; 33(03): 283-287
DOI: 10.1055/a-1679-7225
DOI: 10.1055/a-1679-7225
letter
Iron-Catalyzed Synthesis of Pyridines from α,β-Unsaturated Ketoxime Acetates and N-Acetyl Enamides
We gratefully acknowledge the National Natural Science Foundation of China (22078150), the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture (XTE1826) and the Natural Science Research Projects of Jiangsu Higher Education (19KJB150027) for their financial support.
Abstract
A new method of FeCl2-catalyzed [4+2] annulation of α,β-unsaturated ketoxime acetates with N-acetyl enamides in batch and flow is reported. The current strategy features low-cost catalytic system, use of electron-rich olefins, operational simplicity, and broad substrate scope, thus providing a facile and efficient access to substituted pyridines in moderate to good yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1679-7225.
- Supporting Information
Publication History
Received: 18 October 2021
Accepted: 27 October 2021
Accepted Manuscript online:
27 October 2021
Article published online:
22 November 2021
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- 13 General Procedure for the Synthesis of Pyridines In a sealed tube, ketoxime-enoates 1 (0.2 mmol, 1 equiv), N-acetyl enamides 2 (0.4 mmol, 2 equiv), and FeCl2 (0.02 mmol, 10 mol%) were mixed in DCE (2 mL) and stirred at 120 °C for 8 h. Upon completion of the reaction, the mixture was then allowed to cool down to room temperature and the reaction solution was concentrated under vacuum. The crude residue was purified by column chromatography (petroleum ether/ethyl acetate) on silica gel to give the corresponding pyridines 3. Ethyl 2,6-Diphenylisonicotinate (3aa) Yield 80% (49 mg); white sold; mp 94–95 °C. 1H NMR (400 MHz, CDCl3): d = 8.26 (s, 2 H), 8.21 (dd, J = 8.3, 1.3 Hz, 4 H), 7.55–7.47 (m, 6 H), 4.49 (q, J = 7.1 Hz, 2 H), 1.47 (t, J = 7.1 Hz, 3H) ppm. 13C NMR (100 MHz, CDCl3): d = 165.4, 157.6, 139.3, 138.5, 129.3, 128.6, 126.9, 117.6, 61.7, 14.2 ppm. HRMS (ESI-TOF): m/z calcd for C20H18NO2 [M + H]+:304.1332; found: 304.1345.
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