M. Layek et al. / Tetrahedron Letters 50 (2009) 3867–3871
3871
23. Subramanian, V.; Batchu, V. R.; Barange, D.; Pal, M. J. Org. Chem. 2005, 70,
4778–4783.
Acknowledgements
24. Raju, S.; Batchu, V. R.; Swamy, N. K.; Dev, R. V.; Sreekanth, B. R.; Babu, J. M.;
Vyas, K.; Kumar, P. R.; Mukkanti, K.; Annamalai, P.; Pal, M. Tetrahedron 2006,
62, 9554–9570.
25. Venkataraman, S.; Barange, D. K.; Pal, M. Tetrahedron Lett. 2006, 47, 7317–
7322.
The authors thank Dr. V. Dahanukar and Mr. A. Mukherjee for
their encouragement and the analytical group of DRL for spectral
data. Mr. M.L. thanks CPS-DRL, Hyderabad, India for allowing him
to pursue this work as a part of his Ph.D. programme.
26. (a) General procedure for preparation of 3: A mixture of 8-iodo-4-oxo-1,4-
dihydroquinoline-3-carboxylic acid ethyl ester 1 (300 mg, 0.869 mmol), 10%
Pd/C (9.21 mg, 0.0087 mmol), PPh3 (9.11 mg, 0.034 mmol), CuI (16.55 mg,
0.087 mmol) and Et3N (2.17 mmol) in ethanol (3.0 mL) was stirred for 1 h
under nitrogen. The acetylenic compound 2 (1.30 mmol) was added and the
mixture was stirred at 80 °C for the time mentioned in Table 2. After
completion, the reaction mixture was cooled to room temperature, filtered
through Celite bed and the filtrate was concentrated under vacuum. The crude
mass was diluted with chloroform (30 mL) and water (15 mL) and the mixture
was extracted with chloroform (3 Â 30 mL). The organic layers were collected,
combined, washed with saturated aq NaCl (2 Â 25 mL), dried over anhydrous
Na2SO4 and concentrated under vacuum. The crude compound was purified by
column chromatography on silica gel using 9:1 hexane/ethyl acetate to afford
the desired product 3. (b) Spectral data of selected compounds; compound 3a:
brown solid, mp 131 °C; Rf (90% ethyl acetate/n-hexane) 0.3; 1H NMR (CDCl3,
400 MHz) d 8.94 (s, 1H), 8.0 (d, J = 7.8 Hz, 1H), 7.72 (d, J = 7.3 Hz, 1H), 7.38 (t,
J = 7.6 Hz, 1H), 6.77 (s, 1H), 4.99 (d, J = 3.6 Hz, 2H), 4.35 (q, J = 7.2 Hz, 2H), 3.21
Supplementary data
Supplementary data associated with this article can be found, in
References and notes
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(br s, 1H), 1.39 (t, J = 7.2 Hz, 3H); IR (cmÀ1, KBr)
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IR (cmÀ1, KBr)
m: 3398, 1724, 1621, 1559, 1220; Mass (ES): m/z 286.20 (M+1,
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