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Synlett 2022; 33(19): 1938-1942
DOI: 10.1055/a-1937-9244
DOI: 10.1055/a-1937-9244
letter
Free-Radical-Involved Trifluoromethylthiolation Cyclization of Alkenes To Access SCF3-Substituted Indolo[2,1-a]isoquinolines
Authors
This project is supported by the National Natural Science Foundation of China (21702044, 21971116), the Natural Science Foundation of Hebei Province (B2020201014, B2022201059), the Science and Technology Project of Department of Education of Hebei Province (QN2019063), and the Research Innovation Team of College of Chemistry and Environmental Science of Hebei University (hxkytd-py2102).
Abstract
Free-radical-promoted tandem trifluoromethylthiolation of alkenes with AgSCF3, which provides an efficient protocol for the construction of SCF3-modified indolo[2,1-a]isoquinolines with moderate to good yields. A series of scaled-up experiments, other substrate transformations, and radical inhibition experiments were operated to verify the merit of this reaction system.
Key words
trifluoromethylthiolation - tandem cyclization - alkenes - AgSCF3 - indolo[2,1-a]isoquinolinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1937-9244.
- Supporting Information (PDF)
Publication History
Received: 15 August 2022
Accepted after revision: 06 September 2022
Accepted Manuscript online:
06 September 2022
Article published online:
14 October 2022
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- 18 Typical Procedure for the Synthesis of 5-Methyl-5-{[(trifluoromethyl)thio]methyl}indolo[2,1-a]isoquinolin-6(5H)-one A mixture of 2-methyl-1-(2-phenyl-1H-indol-1-yl)prop-2-en-1-one (1 equiv., 0.1 mmol), AgSCF3 (2 equiv., 0.2 mmol), Na2S2O8 (3 equiv., 0.3 mmol), HMPA (0.6 equiv., 0.06 mmol), and CH3CN (3 mL) was stirred at 80 °C for 12 h under N2. When it was finished, the mixture was condensed under vacuum and purified by column chromatography (petroleum ether/ethyl acetate = 20/1) to access a white solid, 28.9 mg, with an 80% yield. 1H NMR (400 MHz, CDCl3): δ = 8.57 (d, J = 8.0 Hz, 1 H), 7.88 (dd, J = 5.6, 3.2 Hz, 1 H), 7.61 (d, J = 7.6 Hz, 1 H), 7.44–7.34 (m, 5 H), 7.07 (s, 1 H), 3.94 (d, J = 12.4 Hz, 1 H), 3.56 (d, J = 12.4 Hz, 1 H), 1.79 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 170.5, 135.3, 135.2, 134.8, 130.6, 130.3 (q, J = 304.6 Hz), 129.2, 128.3, 126.2, 125.6, 125.0, 124.9, 124.0, 120.6, 116.8, 103.9, 48.6, 39.8, 29.00. 19F NMR (565 MHz, CDCl3): δ = –41.15 (s, 3 F). HRMS (ESI): m/z calcd for C19H15F3NOS [M + H]+: 362.0821; found: 362.0825
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