Sodium borohydride-iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: A facile entry to N-aryl-formylpyrroles

Tetrahedron Letters

Volumn 46, Issue 7, 2005, Pages 1071-1074

  Haldar, Pranab ^a   Guin, Joyram ^a   Ray, Jayanta K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Lactam; Oxidative aromatisation; Pyrrole; Reduction

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; IODINE; METHANOL; PYRROLE DERIVATIVE; SODIUM BOROHYDRIDE;

AROMATIZATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; OXIDATION KINETICS; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION KINETICS; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE;

EID: 12344332759     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.107     Document Type: Article

References (29)

1. J. Lehuede, B. Fauconneau, L. Barrier, M. Ourakow, A. Piriou, and J.M. Vierfond Eur. J. Med. Chem. 34 1999 991 996
2. Nippon Soda Co., Ltd. Japanese Patent 81 79,672, 1981; Chem. Abstr. 1981, 95, 187069f
3. B. Fugmann, F. Lieb, H. Moeschler, K. Naumann, and U. Wachendorff Chem. Unserer Zeit 25 1991 317 330
4. A.R. Battersby Angew. Chem. 107 1995 421 449
5. Angew. Chem., Int. Ed. Engl. 34 1995 383 411
6. C. Kitamura, and Y. Yamashita J. Chem. Soc., Perkin Trans. 1 1997 1443 1448
7. K. Unverferth, J. Engel, N. Hofgen, A. Rostock, R. Gunther, H.J. Lankau, M. Menzer, A. Rolfs, J. Liebscher, B. Muller, and H.J. Hofmann J. Med. Chem. 41 1998 63 73
8. G. Dannhardt, W. Kiefer, G. Kraemer, S. Maehrlein, U. Nowe, and B. Fiebich Eur. J. Med. Chem. 35 2000 499 570
9. R. Rango, G.R. Marshall, R.D. Santo, R. Costi, S. Massa, R. Rompei, and M. Artico Bioorg. Med. Chem. 8 2000 1423 1432
10. M. Artico, R.D. Santo, R. Costi, S. Massa, and A. Retico J. Med. Chem. 38 1995 4223 4233
11. I. Nicolaou, C. Zika, and V.J. Demopoulos J. Med. Chem. 47 2004 2706 2709
12. H.J. Anderson, C.E. Loader, R.X. Xu, N. Le, N.J. Gogan, R. McDonald, and L.G. Edwards Can. J. Chem. 63 1985 896 902
13. N.J. Kevin, J.L. Duffy, B.A. Kirk, K.T. Chapman, W.A. Schleif, D.B. Olsen, M. Stahlhut, C.A. Rutkowski, L.C. Kuo, L. Jin, J.H. Lin, E.A. Emini, and J.R. Tata Bioorg. Med. Chem. Lett. 13 2003 4027 4030
14. G. Sbardella, A. Mai, M. Artico, R. Loddo, M.G. Setzu, and P.L. Colla Bioorg. Med. Chem. Lett. 14 2004 1537 1541
15. A. Thurkauf, J. Yuan, X. Chen, J.W.F. Wasley, R. Meade, K.H. Woodruff, K. Huston, and P.C. Ross J. Med. Chem. 38 1995 4950 4952
16. G.K. Kar, D. Ramesh, B.G. Chatterjee, and J.K. Ray J. Chem. Res. (M). 1997 0568 0583
17. J. Chem. Res. (S) 1997 80 81
18. J.K. Ray, G.K. Kar, B.C. Roy, and N.K. Brahma Bioorg. Med. Chem. 2 1994 1417 1421
19. J.K. Ray, S. Dasadhikari, G.K. Kar, B.C. Roy, and N.K. Brahma Bioorg. Med. Chem. 6 1998 2397 2403
20. B.K. Banik, S. Samajdar, and I. Banik J. Org. Chem. 69 2004 213 216
21. S. Danishefsky, and R.K. Singh J. Am. Chem. Soc. 28 1975 3239 3241
22. P. Haldar, and J.K. Ray Tetrahedron Lett. 44 2003 8229 8231
23. M.J. McKennon, A.I. Meyers, K. Drauz, and M. Schwarm J. Org. Chem. 58 1993 3568 3571
24. A.S.B. Prasad, J.V.B. Kanth, and M. Periasamy Tetrahedron 48 1992 4623 4628
25. J.V.B. Kanth, and M. Periasamy J. Org. Chem. 56 1991 5964 5965
26. Y.H. Wu, and R.F. Feldkamp J. Org. Chem. 26 1961 1519 1524
27. D. Walker, and J.D. Hiebert Chem. Rev. 67 1967 153 165
28. J.A. Ewen, M.J. Elder, R.L. Jones, A.L. Rheingold, L.M. Liable-Sands, and R.D. Sommer J. Am. Chem. Soc. 123 2001 4763 4773
29. M.K. Scott, G.E. Martin, D.L. DiStefano, C.L. Fedde, M.J. Kukla, D.L. Barrett, W.J. Baldy, R.J. Elgin, J.M. Kesslick, J.R. Mathiasen, R.P. Shank, and J.L. Vaught J. Med. Chem. 35 1992 552 558