Acknowledgements
The authors wish to express their gratitude to VIT
Nawaz Khan, F.; Asao, N. Tetrahedron, 2009, 65, 9575-
9582
.
University Vellore for the support and facilities and SIF-VIT
for their support of NMR (DST-FIST Fund), GCMS and IR
facilities. This work was supported by grant No. R0001026
from the Ministry of Trade, Industry & Energy and Busan
Metropolitan City, Korea.
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Typical procedure for the palladium-catalyzed synthesis of 3-
alkynyl-1H-isochromen-1-ones, 3a.
,
38, 2345-2347.
A mix of Pd (OAc)2 (25 mg, 0.11 mmol, 10 mol %),
,
3-chloroisochromen-1-one, 1a (200.45mg, 1.11 mmol), phenyl
acetylene, 2a (1.22 mmol), Ruphos (52mg, 0.11 mmol, 10
mol%) and triethyl amine (224.2 mg, 2.21 mmol) were purged
in a sealed tube with nitrogen gas three times. Then, THF (5.00
mL), water (0.5 mL) was added with a syringe. The reaction
mixture was stirred at 80 °C for 1h and was diluted with ethyl
acetate (30 mL). The mixture was filtered through celite bed
and washed with ethylacetate. The filtrate was concentrated
under reduced pressure and the residue was purified on a silica
gel column using hexane/ethylacetate as eluent to afford the
,
3
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.
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,
desired product. 3a
.
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1
(3a) Light yellow solid, mp 120-122 °C, H-NMR (400 MHz,
CDCl3) δ 8.3 (d, J = 7.90 Hz, 1H), 7.73 (t, J = 7.75 Hz, 1H), 7.56 -
7.51 (m, 3H), 7.45 (d, J = 7.75 Hz, 1H), 7.41 - 7.36 (m, 3H), 6.82
(s, 1H) ppm; 13C NMR (100 MHz, CDCl3) δ 161.8, 138.3, 136.7,
134.9, 131.9, 129.8, 129.7, 129.1, 128.6, 125.8, 121.5, 121.2,
111.4, 93.6, 82.0 ppm; IR (v, cm-1) 3091, 2926, 2854, 2426, 2196,
1737, 1625, 1598, 1564, 1483, 1384, 1336, 1321, 1267, 1236,
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