Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines

Tetrahedron Letters

Volumn 49, Issue 36, 2008, Pages 5302-5308

  Pan, Xiang Qiang ^a   Zou, Jian Ping ^a   Huang, Zhi Hao ^a   Zhang, Wei ^b  

^a SOOCHOW UNIVERSITY   (China)

^b UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 BENZODIOXEPANE DERIVATIVE; ACETOPHENONE; BENZOTHIAZEPINE DERIVATIVE; CHALCONE DERIVATIVE; GALLIUM; GALLIUM TRIFLATE; PHENYLENEDIAMINE;

ARTICLE; DRUG ANALYSIS; DRUG SYNTHESIS; POLYMERIZATION;

EID: 47549116710     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.082     Document Type: Article

References (32)

1. Schutz H. Benzodiazepines (1982), Springer, Heidelberg
2. Landquist J.K. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 1 (1984), Pergamon, Oxford 166-170
3. Randall L.O., and Kappel B. Benzodiazepines. In: Garattini S., Mussini E., and Randall L.O. (Eds) (1973), Raven Press, New York 27
4. Aversa M.C., Ferlazzo A., Gionnetto P., and Kohnke F.H. Synthesis (1986) 230
5. Essaber M., Baouid A., Hasnaoui A., Benharref A., and Lavergne J.P. Synth. Commun. 28 (1998) 4097
6. Xu J.X., Wu H.T., and Jin S. Chin. J. Chem. 17 (1999) 84
7. Zhang X.Y., Xu J.X., and Jin S. Chin. J. Chem. 17 (1999) 404
8. Reddy K.V.V., Rao P.S., and Ashok D. Synth. Commun. 30 (2000) 1825
9. Ried W., and Torinus E. Chem. Ber. 92 (1959) 2902
10. Stahlhofen P., and Ried W. Chem. Ber. 90 (1957) 815
11. Herbert J.A.L., and Suschitzky H. J. Chem. Soc., Perkin Trans. 1 (1974) 2657
12. Morales H.R., Bulbarela A., and Contreras R. Heterocycles 24 (1986) 135
13. Jung D.I., Choi T.W., Kim Y.Y., Kim I.S., Park Y.M., Lee Y.G., and Jung D.H. Synth. Commun. 29 (1999) 1941
14. Balakrishna M.S., and Kaboundin B. Tetrahedron Lett. 42 (2001) 1127
15. Yadav J.S., Reddy B.V.S., Eshwaraian B., and Anuradha K. Green Chem. 4 (2002) 592
16. Curini M., Epifano F., Marcotullio M.C., and Rosati O. Tetrahedron Lett. 42 (2001) 3193
17. Kaboudin B., and Navaee K. Heterocycles 55 (2001) 1443
18. Pozarentzi M., Stephanidou S.J., and Tsoleridis C.A. Tetrahedron Lett. 43 (2002) 1755
19. Reddy B.M., and Sreekanth P.M. Tetrahedron Lett. 44 (2003) 4447
20. Kuo C.W., More S.V., and Yao C.F. Tetrahedron Lett. 47 (2006) 8523
21. Du Y.Y., Tian F.L., and Zhao W.Z. Synth. Commun. 36 (2006) 1661
22. Yan P., Batamack P., Prakash G.K., and Olah G. Catal. Lett. 103 (2005) 165
23. Yan P., Batamack P., Prakash G.K., and Olah G. Catal. Lett. 85 (2003) 1
24. Kobayashi S., Komoto I., and Matsuo J. Adv. Synth. Catal. 343 (2001) 71
25. Yan P., Batamack P., Prakash G.K., and Olah G. Catal. Lett. 101 (2005) 141
26. Deng X.M., Sun X.L., and Tang Y. J. Org. Chem. 70 (2005) 6537
27. Nguyen R.V., and Li C.J. J. Am. Chem. Soc. 127 (2005) 17184
28. Li H.J., Tian H.Y., Wu Y.C., Chen Y.J., Liu L., Wang D., and Li C.J. Adv. Synth. Catal. 347 (2005) 1247
29. Prakash G.K.S., Mathew T., Panja C., Vaghoo H., Venkataraman K., and Olah G.A. Org. Lett. 9 (2007) 179
30. Huang Z.-H., Zou J.-P., and Jiang W.-Q. Tetrahedron Lett. 47 (2006) 7965
31. 4, concentrated to dryness in vacuo, and the residue was purified by column chromatography (eluted with 2:8 EtOAc-petroleum) to afford pure diazepine.
32. 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.