An efcient TBHP/TBAI‑mediated protocol for the synthesis of 4H‑chromen‑4‑ones from…
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funnel. The ethyl acetate layer was sequentially washed with
5% solution of sodium bicarbonate and brine solution. The
combined organic layer was dried over anhydrous Na2SO4,
fltered and concentrated in vacuum. The resulting residue
was purifed over a column of silica gel (100–200 mesh) to
give 2a–2s with petroleum ether/ethyl acetate as the eluent.
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7‑Chloro‑4H‑chromen‑4‑one (2c, C9H5ClO2) M.p.: 148–
1
14. Maho S, Yoshiyuki K (2010) Phytomedicine 17:820
15. Pierre DC, Donatien G, Marguerite T, Bonaventure NT, Pierre P,
Ahmed AA, Amira GM, Godwin AI, Hirata T, Tom MJ (2006)
Nat Prod Commun 1:961
150 °C; H NMR (400 MHz, CDCl3): δ = 8.20 (d, 1H),
7.88 (d, J=6.0 Hz, 1H), 7.64 (dd, 1H), 7.45 (d, 1H), 6.37
(d, J = 6.0 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3):
δ=176.4, 155.4, 154.9, 134.0, 131.3, 125.8, 125.3, 120.0,
113.0 ppm; LC–MS: m/z=178 ([M−2]).
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2‑Phenyl‑4H‑chromen‑4‑one (2h, C15H10O2) M.p.: 95–96 °C;
1H NMR (400 MHz, CDCl3): δ=8.27 (q, J=9.6 Hz, 1H),
7.97–7.95 (m, 2H), 7.72 (d, 1H), 7.62–7.55 (m, 4H), 7.44
(t, J=9.6 Hz, 1H), 6.68 (s, 1H) ppm; 13C NMR (100 MHz,
CDCl3): δ=107.7, 118.1, 124.0, 125.2-125.8, 126.3, 129.1,
131.6–131.9, 133.8, 156.3, 163.4, 178.5 ppm; LC–MS:
m/z=223 ([M+H]+).
18. Sandhya B, Mathew V, Lohitha P, Ashwini T, Shravani A (2010)
Int J Chem PharmaSc 1:16
19. Ankner T, Saxin MF, Pemberton N, Seifert T, Grotli M, Luthman
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21. Mal K, Kaur A, Haque F, Das I (2015) J Org Chem 80:6400
22. Yue Y, Peng J, Wang D, Bian Y, Sun P, Chen C (2017) J Org
Chem 82:5481
7‑Hydroxy‑2‑phenyl ‑4H‑chromen‑4‑one (2i, C15H10O3) M.p.:
1
180–182 °C; H NMR (400 MHz, CDCl3): δ = 7.98–7.96
23. Awuah E, Capretta A (2009) Org Lett 11:3210
24. Nishiraga A, Ando H, Marugama K, Mushino T (1992) Synthesis
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(q, J=5.6 Hz, 3H),7.57–7.54 (m, 4H), 7.36–7.34 (t, J=2.8,
6.0 Hz, 2H), 6.88 (s, 1H) ppm; 13C NMR (100 MHz, CDCl3):
δ=178.5, 163.4, 156.3, 133.8, 131.8, 129.1, 126.3, 125.5,
118.1, 124.0, 107.7 ppm; LC–MS: m/z=239 ([M+H]+).
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Acknowledgements The authors thank Wachemo University, Ethiopia,
for fnancial support to Dr. Habtamu Abebe Agisho and Dr. Suboot
Hairat. Also the author Dr. Mehvash Zaki is highly grateful to King
Abdulaziz University.
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P, Qu LB (2012) Chem Commun 48:10117
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