488
K. Mogilaiah*, J. Uma Rani, B. Sakram and N. Vasudeva Reddy
Vol 43
Table 2
IR and 1H NMR spectral data of [2-Oxo-3-(p-methoxyphenyl)-2H-[1,8]naphthyridin-1-yl]acetic acid arylidenehydrazides (4) and 1-(5-Aryl-
[1,3,4]oxadiazol-2-ylmethyl)-3-(p-methoxyphenyl)-1H-[1,8]naphthyridin-2-ones (5)
Compound
IR cm-1
(KBr)
1H NMR (δ, ppm)
(CDCl3 / CDCl3 + DMSO-d6)
4a
4b
3438 (NH), 1692 (C=O), 3.92 (s, 3H, OCH3), 5.85 (s, 2H, CH2), 8.12 (m, 2H, C4-H, C5-H), 7.85 (m, 1H, C6-H), 8.20
1657 (C=O), 1609 (C=N) (m, 1H, C7-H), 8.63 (s, 1H, N=CH), 6.98-7.80 (m, 9H, Ar-H), 11.02 (s, 1H, CONH)
3436 (NH), 1694 (C=O), 2.40 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 5.80 (s, 2H, CH2), 8.15 (m, 2H, C4-H, C5-H), 7.84 (m,
1652 (C=O), 1609 (C=N) 1H, C6-H), 8.40 (m, 1H, C7-H), 8.60 (s, 1H, N=CH), 6.89-7.78 (m, 8H, Ar-H), 11.05 (s, 1H,
CONH)
4c
4d
4e
4f
3434 (NH), 1690 (C=O), 3.88 (s, 6H, 2xOCH3), 5.81 (s, 2H, CH2), 8.02 (m, 2H, C4-H, C5-H), 7.82 (m, 1H, C6-H),
1660 (C=O), 1605 (C=N) 8.32 (m, 1H, C7-H), 8.63 (s, 1H, N=CH), 6.82-7.78 (m, 8H, Ar-H), 11.06 (s, 1H, CONH)
3440 (NH), 1693 (C=O), 3.93 (s, 3H, OCH3), 5.76 (s, 2H, CH2), 8.22 (m, 2H, C4-H, C5-H), 8.01 (m, 1H, C6-H), 8.50
1658 (C=O), 1616 (C=N) (m, 1H, C7-H), 9.02 (s, 1H, N=CH), 6.92-7.83 (m, 8H, Ar-H), 11.70 (s, 1H, CONH)
3450 (NH), 1692 (C=O), 3.95 (s, 3H, OCH3), 5.78 (s, 2H, CH2), 8.00 (m, 2H, C4-H, C5-H), 7.81 (m, 1H, C6-H), 8.56
1659 (C=O), 1609 (C=N). (m, 1H, C7-H), 8.62 (s, 1H, N=CH), 6.87-7.73 (m, 8H, Ar-H), 11.52 (s, 1H, CONH)
3435 (NH), 1703 (C=O), 3.92 (s, 3H, OCH3), 5.93 (s, 2H, CH2), 8.26 (m, 2H, C4-H, C5-H), 8.00 (m, 1H, C6-H), 8.60
1652 (C=O), 1608 (C=N) (m, 1H, C7-H), 9.08 (s, 1H, N=CH), 6.98-7.82 (m, 8H, Ar-H), 11.08 (s, 1H, CONH)
3439 (NH), 1692 (C=O), 3.93 (s, 3H, OCH3), 5.82 (s, 2H, CH2), 8.21 (m, 2H, C4-H, C5-H), 7.99 (m, 1H, C6-H), 8.56
1652 (C=O), 1608 (C=N) (m, 1H, C7-H), 8.78 (s, 1H, N=CH), 6.92-7.83 (m, 8H, Ar-H), 11.62 (s, 1H, CONH)
3435 (NH), 1690 (C=O), 3.90 (s, 3H, OCH3), 5.86 (s, 2H, CH2), 6.02 (s, 2H, O-CH2-O), 8.26 (m, 2H, C4-H, C5-H),
1658 (C=O), 1609 (C=N) 7.86 (m, 1H, C6-H), 8.48 (m, 1H, C7-H), 8.67 (s, 1H, N=CH), 6.89-7.78 (m, 7H, Ar-H),
11.53 (s, 1H, CONH)
4g
4h
5a
5b
5c
5d
5e
5f
1658 (C=O), 1609 (C=N) 3.90 (s, 3H, OCH3), 6.10 (s, 2H, CH2), 8.18 (m, 2H, C4-H, C5-H), 7.90 (m, 1H, C6-H), 8.42
(m, 1H, C7-H), 6.90-7.69 (m, 9H, Ar-H)
1656 (C=O), 1605 (C=N) 2.42 (s, 3H, CH3), 3.92 (s, 3H, OCH3), 6.02 (s, 2H, CH2), 8.23 (m, 2H, C4-H, C5-H), 8.02 (m,
1H, C6-H), 8.42 (m, 1H, C7-H), 6.92-7.86 (m, 8H, Ar-H)
1660 (C=O), 1604 (C=N) 3.90 (s, 6H, 2xOCH3), 6.00 (s, 2H, CH2), 8.20 (m, 2H, C4-H, C5-H), 7.98 (m, 1H, C6-H),
8.40 (m, 1H, C7-H), 6.90-7.85 (m, 8H, Ar-H)
1658 (C=O), 1607 (C=N) 3.92 (s, 3H, OCH3), 6.03 (s, 2H, CH2), 8.36 (m, 2H, C4-H, C5-H), 7.96 (m, 1H, C6-H), 8.48
(m, 1H, C7-H), 6.96-7.82 (m, 8H, Ar-H)
1665 (C=O), 1612 (C=N) 3.90 (s, 3H, OCH3), 5.98 (s, 2H, CH2), 8.32 (m, 2H, C4-H, C5-H), 7.95 (m, 1H, C6-H), 8.58
(m, 1H, C7-H), 6.93-7.84 (m, 8H, Ar-H)
1659 (C=O), 1610 (C=N) 3.88 (s, 3H, OCH3), 6.03 (s, 2H, CH2), 8.37 (m, 2H, C4-H, C5-H), 8.06 (m, 1H, C6-H), 8.48
(m, 1H, C7-H), 6.96-7.79 (m, 8H, Ar-H)
5g
5h
1658 (C=O), 1610 (C=N) 3.92 (s, 3H, OCH3), 6.08 (s, 2H, CH2), 8.40 (m, 2H, C4-H, C5-H), 8.21 (m, 1H, C6-H), 8.80
(m, 1H, C7-H), 6.98-7.80 (m, 8H, Ar-H)
1659 (C=O), 1609 (C=N) 3.90 (s, 3H, OCH3), 6.02 (s, 2H, O-CH2-O), 6.10 (s, 2H, CH2), 8.37 (m, 2H, C4-H, C5-H),
8.02 (m, 1H, C6-H), 8.56 (m, 1H, C7-H), 6.95-7.80 (m, 7H, Ar-H)
REFERENCES AND NOTES
[1] C. H. Adelstein, G. W. Yen, E. Z. Dajani and R. G.
[11] P. Lidstrom, J. Tierney, B. Wathey and J. Westman,
Tetrahedron., 57, 9225 (2001).
[12] K. Mogilaiah and N.V. Reddy, Synth Commun., 33, 1067
(2003).
Bianchi, J. Med. Chem., 19, 1221 (1976).
[2] R. Kalsi, K. Pande and J. P. Bathwal, Indian J. Chem.,
27B, 197 (1988).
[13] K. Mogilaiah and G.R. Reddy, J. Chem. Res(S)., 145
(2004).
[3] A. K. Dubey and N. K. Sangwan, Indian J. Chem., 33B,
1043 (1994).
[14] K. Mogilaiah and Ch.S. Reddy, Heterocyclic Commun., 10,
363 (2004).
[4] T. Kuroda, F. Suzuki, T. Tamura, K. Ohmori and H.
Hosoe, J. Med. Chem., 35, 1130 (1992).
[15] K. Mogilaiah, G.R. Reddy and Ch. S. Reddy, J. Chem.
Res(S), 832 (2004).
[5] G. Roma, M. D. Braccio, G. Grossi, F. Mattioli and M.
Ghia, Eur. J. Med. Chem., 35, 1021 (2000).
[16] K. Mogilaiah, H. R. Babu and N. V. Reddy, Synth. Commun.,
32, 2377 (2002).
[6] M. Badawneh, P.L. Ferrarini, V. Calderone, C. Manera,
E. Martinotti, C. Mori, G. Saccomanni and L. Testai, J. Med. Chem.,
36, 925 (2001).
[7] A. Cornelis and P. Laszlo, Synthesis, 849 (1980).
[8] R. S. Verma and R. K. Saini, Tetrahedron Lett., 38 2623 (1997).
[9] S. Caddick, Tetrahedron., 51, 10403 (1995)
[10] A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P Jacquault
and D. Mathe, Synthesis., 1213 (1998).
[17] IBD (0.355 g, 10.0 mmol) per gram of neutral
alumina is ground using a pestle and mortar; the recovered
alumina after removal of the products is reused without any
loss of activity.
[18] The design involves piercing the roof of a domestic
microwave oven and as such, proper sealing must be done in order
to avoid the hazards of direct microwave exposure to the
investigator.