A facile preparation of N-protected indolaldehydes using a modified Hass procedure

Tetrahedron Letters

Volumn 46, Issue 47, 2005, Pages 8189-8193

  Mohanakrishnan, Arasambattu K ^a   Balamurugan, Ramalingam ^a   Ramesh, Neelamegam ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Bromomethylindoles; Indolaldehydes; Sodium 2 propane nitronate

Indexed keywords

2 NITROPROPANE; ALDEHYDE; INDOLE DERIVATIVE;

ARTICLE;

EID: 27144534480     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.121     Document Type: Article

References (28)

1. P. Magnus, and T. Gallagher Tetrahedron 37 1981 3889 3897
2. P. Magnus, T. Gallagher, and J.C. Huffman J. Am. Chem. Soc. 104 1982 1140 1141
3. G.W. Gribble, M.G. Saulnier, M.P. Sibi, and J.A. Obaza-Nutaitis J. Org. Chem. 49 1984 4518 4523
4. S. Hibino, E. Sugino, T. Kuwada, N. Ogura, K. Sato, and T. Chosi J. Org. Chem. 57 1992 5917 5921
5. C.-K. Sha, and J.F. Yang Tetrahedron 48 1992 10645 10654
6. B.E. Love, and P.S. Raje J. Org. Chem. 59 1994 3219 3222
7. A.K. Mohanakrishnan, and P.C. Srinivasan J. Org. Chem. 60 1995 1939 1946
8. H. Zhang, and R.C. Larock J. Org. Chem. 67 2002 9318 9330
9. R.S. Kusurkar, S.K. Goswami, and S.M. Vyas Tetrahedron Lett. 44 2003 4761 4763
10. S.P. Kolis, M.T. Clayton, J.L. Grutsch, and M.M. Faul Tetrahedron Lett. 44 2003 5707 5710
11. A.K. Mohanakrishnan, and P.C. Srinivasan Synth. Commun. 25 1995 2407 2414
12. D. Nagarathnam J. Heterocycl. Chem. 29 1992 953 958
13. W. Li, J. Li, D. DeVincentis, and T. Mansour Tetrahedron Lett. 45 2004 1071 1074
14. D.R. Dobson, J. Gilmore, and D.A. Long Synlett 1992 79 80
15. H. Suhana, and P.C. Srinivasan Synth. Commun. 33 2003 3097 3102
16. G. Mehta, and G. Panda Tetrahedron Lett. 38 1997 2145 2148
17. H.H. Muratake, and M. Natsume Heterocycles 29 1999 783 794
18. A.K. Mohanakrishnan, and R. Balamurugan Tetrahedron Lett. 37 2005 2659 2662
19. H.B. Hass, and M.L. Bender J. Am. Chem. Soc. 71 1949 1767 1769
20. T.M. Brown, W. Carruthers, and M.G. Pellatt J. Chem. Soc., Perkin Trans. 1 1982 483 487
21. C.-K. Sha, C.-P. Tsou, Y.-C. Li, R.-S. Lee, F.-Y. Tsai, and R.-H. Yeh J. Chem. Soc., Chem. Commun. 1988 1081 1083
22. C.-K. Sha, and D.-C. Wang Tetrahedron 50 1994 7495 7502
23. T.A. Engler, K. Furness, S. Malhotra, C. Diefenbacher, and J.R. Clayton Tetrahedron Lett. 44 2003 2903 2906
24. S.P. Kolis, M.T. Clayton, J.L. Grutsch, and M.M. Faul Tetrahedron Lett. 44 2003 5707 5710
25. G. Zhu, S.E. Conner, X. Zhou, H.-K. Chan, C. Shih, T.A. Engler, R.S. Al-awar, H.B. Brooks, S.A. Watkins, C.D. Spencer, R.M. Schultz, J.A. Dempsey, E.L. Considine, B.R. Patel, C.A. Ogg, V. Vasudevan, and M.L. Lytle Bioorg. Med. Chem. Lett. 14 2004 3057 3061
26. P. Vanelle, A. Gellis, M. Kaafarani, J. Maldonado, and M.P. Crozet Tetrahedron Lett. 40 1999 4343 4346
27. 4 at reflux.
28. 7S: C, 60.97; H, 4.09; N, 5.69; S, 6.51. Found: C, 61.23; H, 4.15; N, 5.58; S, 6.64.