Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-1,8-diones in PEG

Tetrahedron Letters

Volumn 51, Issue 20, 2010, Pages 2700-2703

  Kidwai, Mazaahir ^a   Bhatnagar, Divya ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

Ceric ammonium nitrate; Homogeneous catalysis; N Substituted decahydroacridine 1,8 dione; Polyethylene glycol; Solvent effects

Indexed keywords

ACRIDINE DERIVATIVE; AMMONIUM NITRATE; CERIC AMMONIUM NITRATE; CERIUM NITRATE; DECAHYDROACRIDINE 1,8 DIONE; MACROGOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ONE POT SYNTHESIS; REACTION OPTIMIZATION; RECYCLING; REPRODUCIBILITY; SOLVENT EFFECT; TEMPERATURE DEPENDENCE;

EID: 77950629546     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.033     Document Type: Article

References (36)

1. Girault S., Grellier P., Berecibar A., Maes L., Mouray E., Lemiere P., Debreu M., Davioud-Charvet E., and Sergheraet C. J. Med. Chem. 43 (2000) 2646-2654
2. Cholody W., Horowska B., Paradziej-Lukowicz J., Martelli S., and Konopa J. J. Med. Chem. 39 (1996) 1028
3. Chen T., Fico R., and Cancellakis E.S. J. Med. Chem. 21 (1978) 868-874
4. Denny W., Atwell G.J., Baguley B.C., and Wakelin L.P.G. J. Med. Chem. 28 (1985) 1568-1574
5. Rewcastle G., Atwell G.J., Chambers D., Baguley B.C., and Denny W.A. J. Med. Chem. 29 (1986) 472-477
6. Tilak B.D., and Ayyangar N.R. Chem. Heterocycl. Compd. 9 (1973) 579
7. Albert A. The Acridines (1966), Edward Arnold Publ., Ltd, London
8. Srividya N., Ramamurthy P., Shanmugasundaram P., and Ramakrishnan V.T. J. Org. Chem. 61 (1996) 5083-5089
9. Dolle F., Hinnen F., Valette H., Fuseau C., Duval R., Peglion J., and Crouzel C. Bioorg. Med. Chem. 5 (1997) 749-764
10. Hernandez-Gallegos Z., Lehman P.A.F., Hong E., Posadas F., and Hernandez-Gallegos E. Eur. J. Med. Chem. 30 (1995) 355-364
11. Martin N., Quinteiro M., Seoane C., Mora L., Suare M., Ockoa E., and Morales A. J. Heterocycl. Chem. 51 (1995) 235-236
12. Wang X.S., Shi D.Q., Zhang Y.F., Wang S.H., and Tu S.J. Chin. J. Org. Chem. 24 (2004) 430-434
13. Tu S.J., Miao C.B., Gao Y., Feng Y.J., and Feng J.C. Chin. J. Org. Chem. 20 (2002) 703-705
14. Li Y.L., Zhang M.M., Wang X.S., Shi D.Q., Tu S.J., Wei X.Y., and Zhong Z.M. J. Chem. Res. (S) (2005) 600
15. Jin T.S., Zhang J.S., Guo T.T., Wang A.Q., and Li T.S. Synthesis (2004) 2001-2005
16. Shi D.-Q., Ni S.-N., Fang Y., Shi J.-W., Dou G.-L., Li X.-Y., and Wang X.-S. J. Heterocycl. Chem. 45 (2008) 653-660
17. Shi D., Ni S., and Dou G. Youji Huaxue 29 (2009) 788-793
18. Chen J., Spear S.K., Huddleston J.G., and Rogers R.D. Green Chem. 7 (2005) 64-72
19. Harris J.M. Poly(ethylene Glycol) Chemistry. Biotechnological Applications (1992), Plenum Press, New York p 3
20. Polyethylene Glycol: Chemistry and Biological Application, ACS Books, Washington, DC, 1998.
21. Mao J., Guo J., Fang F., and Ji S.-J. Tetrahedron 64 (2008) 3905-3911
22. Mukhopadhyay C., and Tapaswi P.K. Tetrahedron Lett. 49 (2008) 6237-6240
23. Kouznetsov V.V., Merchan Arenas D.R., and Bohorquez A.R.R. Tetrahedron Lett. 49 (2008) 3097-3100
24. Itoh K., and Akira Horiuchi C. Tetrahedron 60 (2004) 1671-1681
25. Han B., Jia X.-D., Jin X.-L., Zhou Y.-L., Yang L., Liu Z.-L., and Yu W. Tetrahedron Lett. 47 (2006) 3545-3547
26. Nair V., and Deepthi A. Chem. Rev. 107 (2007) 1862-1891
27. Sridharan V., and Menendez J.C. Org. Lett. 10 (2008) 4303-4306
28. Chang M.-Y., Wu T.-C., Lin C.-Y., and Hung C.-Y. Tetrahedron Lett. 47 (2006) 8347-8350
29. Kidwai M., and Mothsra P. Tetrahedron Lett. 47 (2006) 5029-5031
30. Kidwai M., Mishra N.K., Bansal V., Kumar A., and Mozumdar S. Tetrahedron Lett. 48 (2007) 8883-8887
31. Kidwai M., Bhatnagar D., Mishra N.K., and Bansal V. Catal. Commun. 9 (2008) 2547-2549
32. Venkatesan K., Pujari S.S., and Srinivasan K.V. Synth. Commun. (2009) 228-234
33. Chandrasekhar S., Rao Y.S., Sreelakshmi L., Mahipal B., and Reddy C.R. Synthesis (2008) 1737-1740
34. Das B., Thirupathi P., Mahender I., Reddy V.S., and Rao Y.K. J. Mol. Catal. A: Chem. 247 (2006) 233-239
35. Wang X.-S., Zhang M.-M., Jiang H., Shi D.-Q., Tu S.-J., Wei X.-Y., and Zong Z.-M. Synthesis (2006) 4187-4199
36. 1H NMR, mass spectral, and elemental analysis data). The spectral data for new products are listed.