Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81

Tetrahedron Letters

Volumn 47, Issue 25, 2006, Pages 4253-4257

  Kamal, Ahmed ^a   Shankaraiah, N ^a   Reddy, K Laxma ^a   Devaiah, V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Boron trifluoride diethyletherate; Pyrrolo 2,1 c 1,4 benzodiazepines; Reductive cyclization; Resin cleavage; Solid phase synthesis

Indexed keywords

1,2,3,11A TETRAHYDRO 8 HYDROXY 7 METHOXY 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; ANTIBIOTIC AGENT; AROMATIC COMPOUND; AZIDE; PYRROLO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; REAGENT; RESIN;

ARTICLE; DRUG SYNTHESIS; SOLID; SOLID PHASE SYNTHESIS;

EID: 33646524262     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.025     Document Type: Article

References (45)

1. Fruchtel J.S., and Jung G. Angew. Chem., Int. Ed. 35 (1996) 17
2. Terrett N.K., Gardner M., Gordon W., Kobylecki R.J., and Steele J. Tetrahedron 51 (1995) 8135
3. Nefzi A., Ostresh J.M., and Houghten R.A. Chem. Rev. 97 (1997) 449
4. Ito M., Koyakumaru K., and Takaya T.H. Synthesis (1995) 376
5. Rao H.S.P., and Siva P. Synth. Commun. 24 (1994) 549;
6. Alverez S.G., Fisher G.B., and Singavam B. Tetrahedron Lett. 36 (1995) 2567
7. Molina P., Diaz I., and Tarraga A. Tetrahedron 51 (1995) 5617
8. Ramesha A.R., Bhat S., and Chandrasekaran S. J. Org. Chem. 60 (1995) 7682
9. Capperucci A., Degl' Innocenti A., Funicello M., Mauriello G., Scafato P., and Spagnolo P. J. Org. Chem. 60 (1995) 2254
10. Kamal A., Reddy B.S.P., and Reddy B.S.N. Tetrahedron Lett. 37 (1996) 6803
11. Huang Y., Zhang Y., and Wang Y. Tetrahedron Lett. 38 (1997) 1065
12. Molander G.A. Chem. Rev. 92 (1992) 29
13. Kamal A., Rao M.V., Laxman N., Ramesh G., and Reddy G.S.K. Curr. Med. Chem.: Anti-Cancer Agents 2 (2002) 215
14. Kamal A., Reddy K.L., Devaiah V., Shankaraiah N., and Reddy D.R. Mini-Rev. Med. Chem. 6 (2006) 53
15. Kamal A., Reddy K.L., Devaiah V., Shankaraiah N., and Rao M.V. Mini-Rev. Med. Chem. 6 (2006) 71
16. Kamal A., Reddy G.S.K., and Raghavan S. Bioorg. Med. Chem. Lett. 11 (2001) 387
17. Kamal A., Reddy G.S.K., and Reddy K.L. Tetrahedron Lett. 42 (2001) 6969
18. Kamal A., Reddy G.S.K., Reddy K.L., and Raghavan S. Tetrahedron Lett. 43 (2002) 2103
19. Kamal A., Reddy K.L., Devaiah V., and Reddy G.S.K. Tetrahedron Lett. 44 (2003) 4741
20. Kamal A., Reddy P.S.M.M., and Reddy D.R. Tetrahedron Lett. 43 (2002) 6629
21. Kamal A., Ramana K.V., Ankati H.B., and Ramana A.V. Tetrahedron Lett. 43 (2002) 6861
22. Kamal A., Devaiah V., Reddy K.L., and Shankaraiah N. Adv. Synth. Catal. 348 (2006) 249
23. Shoji E., Toshio S., Tomohiro O., and Yuji M. J. Org. Chem. 61 (1996) 7316
24. Tadamasa O. Tetrahedron Lett. 46 (1971) 4387
25. Thurston D.E. In: Neidle D., and Waring M.J. (Eds). Molecular Aspects of Anticancer Drug DNA Interactions (1993), Macmillan, London 54
26. Kaneko T., Wong H., and Doyle T.W. J. Antibiot. 37 (1984) 300
27. Kamal A., Reddy B.S.P., and Reddy B.S.N. Tetrahedron Lett. 37 (1996) 2281
28. Jones G.B., Davey C.L., Jenkins T.C., Kamal A., Kneale G., Neidle S., Webster G.D., and Thurston D.E. Anticancer Drug Des. 5 (1990) 249
29. Kaneko T., Wong H., and Doyle T.W. Tetrahedron Lett. 24 (1983) 5165
30. Kamal A., Howard P.W., Reddy B.S.N., Reddy B.S.P., and Thurston D.E. Tetrahedron 53 (1997) 3223
31. Thurston D.E., and Bose D.S. Chem. Rev. 94 (1994) 433
32. Kamal A., Rao M.V., and Reddy B.S.N. Khim. Geterotsikl. Seodin. (Chem. Hetreocyl. Compd.) (1998) 1588
33. Kamal A., and Rao N.V. Chem. Commun. (1996) 385
34. 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.
35. Reddy, B. S. P. Ph.D. Thesis, Osmania University, 1995.
36. Kamal A., Reddy K.L., Devaiah V., Shankaraiah N., and Reddy Y.N. Tetrahedron Lett. 45 (2004) 7667
37. Kamal A., Reddy K.L., Devaiah V., and Shankaraiah N. Synlett (2004) 2533
38. Kamal A., Reddy K.L., Devaiah V., and Shankaraiah N. Synlett (2004) 1841
39. Kamal A., Reddy K.L., Reddy G.S.K., and Reddy B.S.N. Tetrahedron Lett. 45 (2004) 3499
40. Kamal A., Ramana A.V., Reddy K.S., Ramana K.V., Babu A.H., and Prasad B.R. Tetrahedron Lett. 45 (2004) 8187
41. Kamal A., Ramana K.V., and Rao M.V. J. Org. Chem. 66 (2001) 997
42. Mhaske S.B., and Argade N.P. J. Org. Chem. 66 (2001) 9038
43. Kamal A., Reddy B.S.P., and Reddy B.S.N. Tetrahedron Lett. 37 (1996) 2281
44. Mayers A.I., Comins D.L., Roland D.M., Henning R., and Shimizu K. J. Am. Chem. Soc. 101 (1979) 7104
45. Barn D.R., Morphy J.R., and Rees D.C. Tetrahedron Lett. 37 (1996) 3213