A. Kamal et al. / Tetrahedron Letters 42 (2001) 6969–6971
6971
O
CCl3
OH
i
NH
1
2
X
X
COOCH3
O
COOCH3
OH
ii
R
R
2
+
N
N
O
O
4
3
iii
H
O
H
O
H
N
N
H
R
iv
R
N
N
OH
6
O
O
O
5
R = OCH3, OBn
X = NO2, N3
Scheme 1. (i) Trichloroacetonitrile, DBU, CH2Cl2, 40 min, 0°C; (ii) Trifluoromethanesulphonic acid, CH2Cl2, 10 min; (iii)
Indium/NH4Cl, DMF or EtOH, reflux for 3 h; (iv) TFA/CH2Cl2 (1:3).
Acknowledgements
Drug Des. 1990, 5, 249; (d) Kaneko, T.; Wong, H.;
Doyle, T. W. Tetrahedron Lett. 1983, 24, 5165.
7. Kamal, A.; Howard, P. W.; Reddy, B. S. N.; Reddy, B.
S. P.; Thurston, D. E. Tetrahedron 1997, 53, 3223.
8. (a) Thurston, D. E.; Bose, D. S. Chem. Rev. 1994, 94,
433; (b) Kamal, A.; Rao, M. V.; Reddy, B. S. N. Khim.
Getero. Seod. (Chem. Het. Compd.) 1998, 1588; (c)
Kamal, A.; Rao, N. V. Chem. Commun. 1996, 385.
9. (a) Carbateas, P. M. US Patent 3,732,212, 1973; Chem.
Abstr. 1973, 79, P42570x, US Patent 3,763,183, 1973;
Chem. Abstr. 1973, 79, P146567t, US Patent 3,860,600,
1975; Chem. Abstr. 1975, 83, P58892x; (b) Reddy, B. S. P.
Ph.D. Thesis, Osmania University, 1995.
The authors (G.S.K.R and K.L.R.) are thankful to
CSIR (New Delhi) for the award of Senior and Junior
Research Fellowships, respectively.
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13. Spectral data for 6g: 1H NMR (200 MHz, CDCl3): l
2.0–2.1 (m, 1H), 2.7–2.9 (m, 1H), 3.5–3.6 (m, 1H), 3.8–3.9
(m, 1H), 3.9 (s, 6H), 4.1–4.2 (t, 1H), 4.4–4.5 (m, 1H), 6.6
(s, 1H), 7.5 (s, 1H), 10.0 (brs, 1H), MS (EI) m/z 292.