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Synlett 2024; 35(13): 1572-1576
DOI: 10.1055/a-2216-4882
DOI: 10.1055/a-2216-4882
letter
Sulfur-Mediated ipso-Cyclization of 4-(p-Methoxyaryl)alk-1-ynes Leading to 3-Thiospiro[4.5]deca-1,6,9-trien-8-ones
This work is supported by the Natural Science Foundation of Beijing Municipality (2202040).
Abstract
A new method for the intramolecular electrophilic ipso-cyclization of alkynes with triflic anhydride-activated sulfoxides, followed by demethylation with triethylamine in one pot, is described for the synthesis of 3-thiospiro[4.5]-decatrienones in moderate to good yields. This method provides a facile strategy for assembling the sulfur-substituted spirocyclic compounds.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2216-4882.
- Supporting Information
Publikationsverlauf
Eingereicht: 30. Oktober 2023
Angenommen nach Revision: 22. November 2023
Accepted Manuscript online:
22. November 2023
Artikel online veröffentlicht:
11. Januar 2024
© 2024. Thieme. All rights reserved
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- 21 1-Phenyl-2-(phenylsulfanyl)spiro[4.5]deca-1,6,9-trien-8-one (3aa-1); Typical Procedure A flame-dried Schlenk tube was charged with alkyne 1a (0.15 mmol, 1.0 equiv) and PhS(=O)Me (2; 0.3 mmol, 2.0 equiv). The reactants were dissolved in CH2Cl2 (2 mL) under N2, and the solution was cooled to –78 °C (liquid N2–EtOAc bath), then 2-chloropyridine (28 μL, 0.3 mmol, 2.0 equiv) and Tf2O (50 μL, 0.3 mmol, 2.0 equiv) were added dropwise. The mixture was stirred at –78 °C for 0.5 h and then Et3N (0.199 mL, 1.5 mmol, 10.0 equiv) was added. When the reaction was complete, the mixture was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel) to give a white solid; yield: 37.6 mg (74%); Rf = 0.2 (PE–EtOAc, 10:1). 1H NMR (400 MHz, CDCl3): δ = 7.46–7.42 (m, 2 H), 7.37–7.30 (m, 3 H), 7.28–7.24 (m, 3 H), 7.23–7.19 (m, 2 H), 6.97 (d, J = 10.1 Hz, 2 H), 6.25 (d, J = 10.1 Hz, 2 H), 2.66 (t, J = 7.1 Hz, 2 H), 2.19 (t, J = 7.2 Hz, 2 H). 13C NMR (101 MHz, CDCl3): δ = 185.2, 152.5, 139.8, 137.2, 134.2, 132.2, 132.0, 128.7, 128.3, 127.6, 127.5, 57.7, 35.5, 34.9. HRMS (ESI): m/z [M + H]+ calcd for C22H19OS: 331.1152; found: 331.1157.