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Synlett 2022; 33(11): 1097-1101
DOI: 10.1055/a-1828-7504
DOI: 10.1055/a-1828-7504
letter
Regioselective Construction of Coumarin-1,2,4-triazines via a Cs2CO3-Catalyzed [3+3] Cycloaddition Reaction
Autoren
This work is supported by the National Natural Science Foundation of China (92156025, 21901181, and 21961142015) and the National Key Research and Development Program of China (2019YFA0905100).
Abstract
A cesium carbonate (Cs2CO3)-catalyzed [3+3] cycloaddition reaction of coumarin-diazo reagents with glycine imino esters is established to produce tetrahydro-1,2,4-triazines in good yields with excellent regioselectivity. One-pot cycloaddition/oxidation protocol could further provide practical access to a series of new coumarin-decorated 1,2,4-triazines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1828-7504.
- Supporting Information (PDF) (opens in new window)
- CIF File (ZIP) (opens in new window)
Publikationsverlauf
Eingereicht: 10. März 2022
Angenommen nach Revision: 19. April 2022
Accepted Manuscript online:
19. April 2022
Artikel online veröffentlicht:
06. Mai 2022
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- 10 Typical Experimental Procedure for the Cs2CO3-Catalyzed [3+3] Cycloaddition Reaction A 10 mL Schlenk tube equipped with a stirring bar and capped with a rubber septum was charged with coumarin-diazo reagents (1, 1.0 equiv., 0.2 mmol), glycine imino ester (2, 1.5 equiv., 0.3 mmol), Cs2CO3 (0.2 equiv., 0.04 mmol, 13 mg). CH2Cl2 (2.0 mL) was transferred into the tube. The reaction mixture was stirred under an air atmosphere at rt for 12 h. After the reaction completed (detected by TLC), the reaction mixture was purified by flash chromatography on silica gel (eluting with ethyl acetate/petroleum ether = 1:1) to give the desired product 3. Characterization Data for Compound 3a Obtained as a yellow solid after column chromatography (EtOAc/petroleum ether = 2:1, Rf = 0.5), 83.3 mg, 93% yield, mp 145–147 °C. 1H NMR (600 MHz, CDCl3): δ = 8.52–8.49 (m, 1 H), 7.82–7.80 (m, 1 H), 7.66–7.61 (m, 2 H), 7.49 (d, J = 8.8 Hz, 1 H), 7.27–7.17 (m, 3 H), 7.12 (d, J = 8.1 Hz, 2 H), 6.56 (s, 1 H), 5.87 (s, 1 H), 5.73 (d, J = 3.4 Hz, 1 H), 4.78–4.63 (m, 1 H), 4.23–4.10 (m, 1 H), 3.95 (s, 3 H) ppm. 13C NMR (151 MHz, CDCl3): δ = 162.1, 160.4, 152.5, 151.1, 136.5, 135.9, 135.1, 134.6, 129.4, 129.3, 128.3, 127.7, 127.5, 124.4, 123.2, 122.8, 119.2, 115.0, 113.1, 59.5, 56.0, 53.4 ppm. HRMS (ESI-TOF): m/z [M + H] calcd for C24H19N3O4Cl: 448.1064; found: 448.1064.
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