A New and Direct Synthesis of Chalcones Via TFAA-H3PO4 Mediated
Letters in Organic Chemistry, 2011, Vol. 8, No. 1
59
2H, J = 8.8 Hz); 13CNMR (CDCl3, 100 MHz) ꢀ 13.8, 19.2,
31.1, 67.9 (OCH2), 34.6 (CH2), 114.2 (aromatic C), 121.9
(aromatic C), 128.3 (aromatic C), 128.5 (aromatic C), 128.8,
129.2, 130 130.3 (aromatic C), 130.2 (aromatic C), 130.3,
131.3, (aromatic C), 135.1 (aromatic C), 143.8 (=CH), 163.0
(=CH), 188.6 (CO); IR (KBr) vmax/cm-1: 2957, 1655 (CO),
1600 (C=C), 1572 (C=C), 1256 (C-O), 829, 764, (bending);
Mass (ESI) 281.20 (M+1, 100%); Anal. calcd for C19H20O2
C 81.40; H 7.19; Found C 81.14; H 7.11.
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1
Compound 3g: Pale yellow solid; HNMR (CDCl3, 400
MHz): ꢀ 0.88 (t, 3H, J = 7.0 Hz), 1.26-1.48 (m, 14H), 1.81
(m, 2H), 4.04 (t, 2H, J = 6.6 Hz), 6.96 (d, 2H, J = 8.8 Hz),
7.41 (m, 3H), 7.54 (d, 1H, J = 15.8 Hz), 7.64 (m, 2H), 7.80
(d, 1H, J = 15.7 Hz), 8.03 (d, 2H, J = 8.8 Hz); 13CNMR
(CDCl3, 100 MHz) ꢀ 14.1 22.6, 26.0, 31.9, 68.2 (OCH2),
114.2 (aromatic C), 121.8 (aromatic C), 128.3 (aromatic C),
128.4 (aromatic C), 128.8, 129.3 (aromatic C), 130.2
(aromatic C), 130.7, 135.1 (aromatic C), 143.8 (=CH), 163.0
(=CH), 188.6 (CO); IR (KBr) vmax/cm-1: 2922, 2850, 1656
(CO), 1606 (C=C), 1575 (C=C), 1273 (C-O), 829, 764
(bending); Mass (ESI) 365.30 (M+1, 100%); Anal. calcd for
C25H32O2 C 82.37; H 8.85; Found C 82.06; H 8.94.
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ACKNOWLEDGEMENT
Smyth, T.P.; Corby, B.W. Toward
a clean alternative to
The authors (K. K. and S. P.) thank Mr. M. N. Raju, the
chairman of MNR Educational Trust for constant support
and encouragement.
friedelꢃcrafts acylation: in situ formation, observation, and reaction
of an acyl bis(trifluoroacetyl)phosphate and related structures. J.
Org. Chem., 1998, 63, 8946-8951.
Veeramaneni, V. R.; Pal, M.; Yeleswarapu, K. R. A high speed
parallel synthesis of 1,2-diaryl-1-ethanones via a clean-chemistry
C–C bond formation reaction. Tetrahedron, 2003, 59, 3283-3290.
Pal, S.; Bindu, P.; Venna, P. R.; Dubey, P. K. Novel naproxen
derivatives: lewis acid/transition-metal free synthesis via C-C bond
forming reaction. Lett. Org. Chem., 2007, 4, 292-295.
Pal, S.; Khan, M. A.; Bindu, P.; Dubey, P. K. Transition-
metal/Lewis acid free synthesis of acyl benzothiophenes via C-C
bond forming reaction. Beilstein J. Org. Chem., 2007, 3, 35,
doi:10.1186/1860-5397-3-35.
Kavitha, K.; Reddy, V. R.; Mukkanti, K.; Pal, S. A TFAA–H3PO4-
mediated direct, metal-free and high-speed synthesis of aryl
carboxylate esters from phenols. J. Fluorine Chem., 2009, 130,
505-508.
For preparation of 2-chloroquinolin-3-aldehyde, see: Meth-Cohn,
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The (E)-3-(2-chloroquinolin-3-acylic acid was prepared according
to a similar procedure reported in the literature, see for example:
Brown, T.H.; Blakemore, R.C.; Blurton, P.; Durant, G.J.; Ganellin,
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