6892
P. D. Lokhande et al. / Tetrahedron Letters 48 (2007) 6890–6892
NH HCl
2. Lokhande, P. D.; Kuchekar, B. S.; Chabukswar, A. R.;
Jagdale, S. C. Asian J. Biochem. 2006, 1, 1–17.
OH
2
OH
HCl
R
R
NH+
3. Kuroda, T.; Goto, H.; Ishikawa, T. Indazole derivatives,
Jpn. Kokai Tokkyo Koho, Japanese Patent, 50130759,
R
1
975; Chem. Abstr. 85, 46631.
4
. Banno, K.; Kawahata, T.; Ikeda, T.; Nakagawa, K.; Dohi,
T., Japanese Patent , 48048407, 1973; Chem. Abstr. 1973,
R
NNH2
7
9, 92214.
5
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Chem. Lett. 1996, 6, 2916.
NH HCl
O
R
2
6
. Behr, L. C.; Fusco, R.; Jarbose, C. H. Chem. Heterocycl.
Comp. 1967, 22, 1.
R
NH
7
. Baiocchi, G.; Corsi, G.; Palazzo, G. Synthesis 1978,
6
33.
8. Szmant, H. H.; Harmayth, C. J. Am. Chem. Soc. 1959, 81,
62.
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1. Krishnan, R.; Lang, S. A.; Lin, Y. I.; Wilkinson, R. G.
J. Heterocycl. Chem. 1988, 25, 447.
9
9
(
OH
+
H
1
1
N-H
NH
N-H
R
N
H
+
1
2. Rakib, E. M.; Benchidmi, M.; Essass, E. M.; Bouadil, A.
E.; Mansour, A. I.; Bellan, J.; Lopaz, L.; Lamande, L. Ind.
J. Chem. B 2000, 39, 339.
R
R
1
3. Cheng, C. Y.; Mo, M.; Grima, J.; Saso, L.; Tita, B.;
Mruk, D.; Silvestrini, B. Contraception 2002, 65, 265.
4. (a) Silvestrini, R.; Caputo, A. Oncology 1984, 412; (b)
Gasperi, C.; Roncuzzi, L.; Zoli, Lo.; Amadoni, D.
Anticancer Drug Des. 1997, 12, 91.
1
N-H
N
R
1
5. Dell’erba, C. l.; Novi, M.; Petrillo, G.; Tsavani, C.
Tetrahedron 1994, 50, 3529.
1
6. (a) Bartsch, R. A.; Yang, I. W. J. Heterocycl. Chem. 1984,
21, 1063; (b) Sun, J. H.; Teleha, C. A.; Yan, J. S.; Rodgers,
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J. Org. Chem. 2005, 70, 596.
R
Scheme 3. Proposed mechanism for the synthesis of indazoles from
substituted salicylaldehydes.
1
1
1
2
8. Auwers, K. V.; Ernecke, A.; Wolter, E. Ann 1930, 478,
refluxed for 2–3 h and the solvent was distilled under
reduced pressure. Purification of the residue by filtration
through a pad of silica afforded indazole 3 as a yellow
solid. The products were characterized from spectral
1
54.
9. Fujimura, Y.; Shiraki, Y.; Nawata, Y.; Matsunaga, I.
Yakugaku Zasshi 1986, 106, 1002.
1
0. H NMR data of new compounds: (i) 5-(Diethylamino)-1-
2
0
1
data and melting points.
H-indazole (Table 2, entry 15), mp 102 °C H NMR
(
3
CDCl ) d 8.01 (s,1H), 7.75 (s,1H), 7.58 (d, J = 8.6 Hz,
1
H), 7.43 (dd, J = 8.6, 1.5 Hz, 1H), 5.2 (s, 1H), 3.2 (q,
References and notes
J = 4H), 1.03 (t, J = 6H); (ii) 5-(diethylamino)-1-pheny-
lindazole (Table 2, entry 16), mp 152 °C H NMR
3
(CDCl ) d 8.00 (s, 1H), 7.63 (s, 1H), 7.58 (d, 1H,
J = 8.6 Hz, 1H) 7.52 (dd, J = 8.6, 1.5H), 7.42 (m, 5H),
3.2 (q, J = 4H), 1.03 (t, J = 6H).
1
1
. (a) Gaikwad, D. D. M.Phil Thesis, University of Pune,
003; (b) Lokhande, P. D.; Waghmare, B. Y.; Sakate, S. S.
Ind. J. Chem. B 2005, 44, 2338.
2