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DOI: 10.1055/s-0029-1219778
Copper(I)-Catalyzed Synthesis of Polysubstituted Furans from Alkynoates and 1,3-Dicarbonyl Compounds in the Presence of Oxygen
Publication History
Publication Date:
17 March 2010 (online)
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Abstract
A novel and straightforward synthesis of polysubstituted furans was achieved easily from the oxidative cyclization of 1,3-dicarbonyl compound and alkynoate catalyzed by CuI in the presence of O2.
Key words
polysubstituted furans - oxidant - copper catalysis - oxygen.
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
General Procedure
for the Preparation of Dimethyl But-2-yndioate and 1,3-Diphenyl-1,3-propanedione
(3aa)
An oven-dried Schlenk tube was charged with
CuI (9.5 mg, 0.05 mmol), 1a (0.50 mmol),
and 2a (0.50 mmol). The Schlenk tube was
sealed and then evacuated and backfilled with oxygen (3 cycles).
Then DMF (2 mL) was added to the reaction system. The reaction was
stirred at 110 ˚C under O2 (1 atm)
for 4 h. After cooling to r.t., the solvent diluted with Et2O
(10 mL) and washed with brine (5 mL) and dried over anhyd Na2SO4.
After the solvent was evaporated in vacuo, the residues were purified
by column chromatography, eluting with PE-EtOAc (10:1)
to afford pure 3aa.
Dimethyl 4-Benzoyl-5-phenylfuran-2, 3-dicarboxylate (3aa)
Yellow
viscous oil. ¹H NMR (400 MHz CDCl3): δ = 3.61
(s, 3 H), 3.96 (s, 3 H), 7.29-7.39 (m, 5 H), 7.50-7.54
(m, 1 H), 7.61-7.63 (m, 2 H), 7.79-7.81 (m, 2
H). ¹³C NMR (100 MHz, CDCl3): δ = 52.4,
52.5, 121.5, 126.2, 127.4, 127.6, 128.5, 128.6, 129.3, 130.2, 133.6,
136.7, 141.1, 155.3, 157.7, 161.9, 190.0. IR (neat): 694, 772, 899,
1080, 1167, 1235, 1443, 1666, 1730, 2953, 3004, 3062 cm-¹.
HRMS (EI): m/z calcd for C21H16O6 [M + H]+:
365.1020; found: 365.1029.
The ¹H NMR, ¹³C
NMR, IR, and HRMS data of 3aa-bb can be found in the Supporting Information.