5308
X.-Q. Pan et al. / Tetrahedron Letters 49 (2008) 5302–5308
O
SH
Ga(OTf)3
no reaction
no reaction
+
or
or
NH2
OH
O
SH
Ga(OTf)3
+
NH2
Scheme 2. Reaction condition: chalcone (1.0 equiv), aniline, or thiophenol (1.1 equiv), Ga(OTf)3 (10 mol %), CH3CN, room temperature, 6 h.
Green Chem. 2002, 4, 592; (f) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati,
Acknowledgement
O. Tetrahedron Lett. 2001, 42, 3193; (g) Kaboudin, B.; Navaee, K. Heterocycles
2001, 55, 1443; (h) Pozarentzi, M.; Stephanidou, S. J.; Tsoleridis, C. A.
Tetrahedron Lett. 2002, 43, 1755; (i) Reddy, B. M.; Sreekanth, P. M.
Tetrahedron Lett. 2003, 44, 4447; (j) Kuo, C. W.; More, S. V.; Yao, C. F.
Tetrahedron Lett. 2006, 47, 8523; (k) Du, Y. Y.; Tian, F. L.; Zhao, W. Z. Synth.
Commun. 2006, 36, 1661.
J.P.Z. thanks the financial support from National Natural Science
Foundation of China (No. 20772088).
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16. A general procedure for synthesis of 2,2,4-trisubstituted-1,5-benzodiazepines 2
Supplementary data
Supplementary data associated with this article can be found, in
References and notes
1. (a) Schutz, H. Benzodiazepines; Springer: Heidelberg, 1982; (b) Landquist, J. K..
In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.;
Pergamon: Oxford, 1984; Vol. 1, pp 166–170.
2. Randall, L. O.; Kappel, B. Benzodiazepines. In Garattini, S., Mussini, E., Randall, L.
O., Eds.; Raven Press: New York, 1973; p 27.
3. (a) Aversa, M. C.; Ferlazzo, A.; Gionnetto, P.; Kohnke, F. H. Synthesis 1986, 230;
(b) Essaber, M.; Baouid, A.; Hasnaoui, A.; Benharref, A.; Lavergne, J. P. Synth.
Commun. 1998, 28, 4097; (c) Xu, J. X.; Wu, H. T.; Jin, S. Chin. J. Chem. 1999, 17,
84; (d) Zhang, X. Y.; Xu, J. X.; Jin, S. Chin. J. Chem. 1999, 17, 404; (e) Reddy, K. V.
V.; Rao, P. S.; Ashok, D. Synth. Commun. 2000, 30, 1825.
(Table 2):
A mixture of o-phenylenediamine (2 mmol), acetophenone
(4.5 mmol), and Ga(OTf)3 (0.2 mmol) in 10 mL of MeCN was stirred at room
temperature for 5–6 h. After completion of the reaction (TLC analysis), the
reaction mixture was diluted with water, and extracted with dichloromethane
(2 ꢁ 10 mL). The combined organic layer was dried over Na2SO4, concentrated
to dryness in vacuo, and the residue was purified by column chromatography
(eluted with 2:8 EtOAc–petroleum) to afford pure diazepine.
17. A general procedure for synthesis of 2,4-disubstituted-1,5-benzodiazepines and
4. Ried, W.; Torinus, E. Chem. Ber. 1959, 92, 2902.
5. Stahlhofen, P.; Ried, W. Chem. Ber. 1957, 90, 815.
2,4-disubstituted-1,5-benzothiaze-pines
5
(Table 3):
A
mixture of o-
aminothiophenol (1.1 mmol), chalcone (1 mmol), and Ga(OTf)3 (0.1 mmol) in
10 mL of MeCN was stirred at 60 °C for an appropriate time. After completion
of the reaction (TLC analysis), the residue was purified by column
chromatography (eluted with 2:8 EtOAc–petroleum ether) to afford pure
thiadiazepine.
6. (a) Herbert, J. A. L.; Suschitzky, H. J. Chem. Soc., Perkin Trans. 1 1974, 2657; (b)
Morales, H. R.; Bulbarela, A.; Contreras, R. Heterocycles 1986, 24, 135; (c) Jung,
D. I.; Choi, T. W.; Kim, Y. Y.; Kim, I. S.; Park, Y. M.; Lee, Y. G.; Jung, D. H. Synth.
Commun. 1999, 29, 1941; (d) Balakrishna, M. S.; Kaboundin, B. Tetrahedron Lett.
2001, 42, 1127; (e) Yadav, J. S.; Reddy, B. V. S.; Eshwaraian, B.; Anuradha, K.