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Synlett 2023; 34(20): 2417-2422
DOI: 10.1055/a-2123-7565
DOI: 10.1055/a-2123-7565
cluster
Special Issue Dedicated to Prof. Hisashi Yamamoto
Acid-Catalyzed [4+1]-Dearomatization Spiroannulation of Hydroquinones and Naphthols
Authors
Financial support for this work was generously provided by ShanghaiTech University.
Dedicated to the 80th birthday of Professor Hisashi Yamamoto.
Abstract
Acid-catalyzed [4+1]-dearomatization spiroannulation reactions of electron-rich hydroquinone and naphthol derivatives were demonstrated as convenient methods to access spirocyclic cyclohexadienone derivatives. The Lewis acid Bi(OTf)3 exhibited the best catalytic performance when a 1,2-dialkynylbenzene was used as the electrophile for the spiroannulation, whereas the Brønsted acid benzene-1,2-disulfonic acid was the best catalyst when 2-ethynylbenzylic esters were used as electrophiles. Most of the reaction conditions are mild, efficient, and simple to operate.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2123-7565.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 30. April 2023
Angenommen nach Revision: 05. Juli 2023
Accepted Manuscript online:
05. Juli 2023
Artikel online veröffentlicht:
29. August 2023
© 2023. Thieme. All rights reserved
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References and Notes
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3′-Hydroxy-1,3-bis(methylene)-1,3-dihydro-2′H-spiro[indene-2,1′-naphthalen]-2′-one (3af): Typical Procedure
1a (0.2 mmol, 1.0 equiv) was added to a solution of Bi(OTf)3 (0.01 mmol, 5 mol%), AcOH (0.4 mmol, 2.0 equiv), and 2f (0.3 mmol, 1.5 equiv) in CHCl3 (1 mL), and the mixture was stirred at 60 °C for 2 h. When the reaction was complete (TLC), the mixture was cooled to rt and the reaction was quenched with sat. aq NaHCO3. The aqueous layer was extracted with CH2Cl2 (×3), and the combined organic layers were washed with brine, dried (Na2SO4), and concentrated by rotary evaporation. The crude product was purified by column chromatography [silica gel, PE–EtOAc (95:5)] to give a yellow solid; yield: 44.1 mg (77%); mp 165–167 °C.IR (neat): 3411, 3017, 1662, 1627, 1400, 1225, 1166, 883, 750 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.55 (dd, J = 5.8, 3.1 Hz, 2 H), 7.30 (dd, J = 5.8, 3.1 Hz, 2 H), 7.23–7.14 (m, 2 H), 7.04 (ddd, J = 8.5, 5.8, 3.0 Hz, 1 H), 6.91–6.77 (m, 2 H), 6.25 (s, 1 H), 5.51 (s, 2 H), 4.67 (s, 2 H). 13C NMR (101 MHz, CDCl3): δ = 195.2, 152.0, 144.5, 141.3, 141.2, 130.4, 129.7, 128.4, 127.9, 127.8, 127.6, 121.7, 118.3, 106.3, 66.2. HRMS (ESI): m/z [M + H]+ calcd for C20H15O2: 287.1072; found: 287.1062. - 32 Li R, Wang SR, Lu W. Org. Lett. 2007; 9: 2219
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