The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.
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D. A. Horton, G. T. Bourne, and M. L. Smythe, Chem. Rev., 103, 893 (2003).
R. J. Sundberg, Indoles, Academic Press, San Diego (1996).
G. R. Humphrey and J. T. Kuethe, Chem. Rev., 106, 2875 (2006).
K. Sukata, Bull. Chem. Soc. Jpn., 56, 280 (1983).
W. C. Guda and D. J. Mathre, J. Org. Chem., 45, 3172 (1980).
M. G. Reinecke, J. F. Sebastian, H. W. Jonson, Jr., and C. Pyun, J. Org. Chem., 37, 3066 (1972).
B. Cardillo, G. Casnati, A. Pochini, and A. Ricca, Tetrahedron, 23, 3771 (1967).
G. M. Rubottom and J. C. Chabala, Synthesis, 566 (1972).
E. Santaniello, C. Farach, and F. Pointi, Synthesis , 617 (1979).
A. Barco, S. Benetti, and G. P. Pollini, Synthesis, 124 (1976).
V. Bocchi, G. Casnati, and A. Dossena, Synthesis, 414 (1976).
Y. R. Jorapur, J. M. Jeong, and D. Y. Chi, Tetrahedron Lett., 47, 2435 (2006).
G. Vavilina, A. Zicmanis, S. Drozdova, P. Mekss, and M. Klavins, Khim. Geterotsikl. Soedin., 676 (2008). [Chem. Heterocycl. Comp., 44, 530 (2008)].
H. Normant and T. Cuvigny, Bull. Soc. Chim. Fr., 1866 (1965).
D. M. Fink, Synlett, 2396 (2004).
S. Hayat, Atta-ur-Rathman, M. I. Choudhary, K. M. Khan, W. Schumann, and E. Bayer, Tetrahedron, 50, 9951 (2001).
T. Kunieda and B. Witkop, J. Org. Chem., 35, 3981 (1970).
D. Bogdal, J. Pielichowski, and K. Jaskot, Heterocycles, 45, 715 (1991).
C. Najera and M. Yus, Tetrahedron, 55, 10547 (1999).
P. Hamel, Y. Girard, and J. Atkinson, J. Org. Chem., 57, 2695 (1992).
J. Atkinson, P. Hamel, and Y. Girard, Synth. Commun., 480 (1988).
G. Broggini, D. Diliddo, and G. Zecchi, J. Heterocycl. Chem., 28, 89 (1991).
B. M. Trost and D. P. Curran, Tetrahedron Lett., 22, 1289 (1981).
K. C. Kumara Swamy, N. N. Bhuvan Kumar, E. Balaraman, and K. V. P. Pavan Kumar, Chem. Rev., 109, 2551 (2009).
N. E. Golantsov, A. V. Karchava, Z. A. Starikova, F. M. Dolgushin, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 1540 (2005). [Chem. Heterocycl. Comp., 41, 1290 (2005)].
S. S. Bhagwat and C. Guck, Tetrahedron Lett., 35, 3477 (1994).
S. Caddick, C. L. Shering, and S. N. Wadman, Tetrahedron Lett., 56, 469 (2006).
A. Bombur and G. Casi, Tetrahedron Lett., 43, 2187 (2002).
T. Tsunoda and T. Yamanya, Tetrahedron Lett.¸ 34, 1640 (1993).
G. H. Lee, I. K. Youn, E. B. Choi, H. K. Lee, G. H. Yon, H. C. Yang, and C. S. Pak, Curr. Org. Chem., 8, 1263 (2004).
A. C. Brown and L. A. Carpino, J. Org. Chem., 50, 1749 (1985).
G. H. Lee, E. B. Choi, E. Lee, and C. S. Pak, Tetrahedron Lett., 28, 4541 (1993).
W. A. Bonner, J. Am. Chem. Soc., 74, 1034 (1952).
R. Mozingo, D. E. Wolf, S. A. Harris, and K. Folkers, J. Am. Chem. Soc., 65, 1013 (1943).
A. V. Kurkin, D. S. Belov, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 1391 (2008). [Chem. Heterocycl. Comp., 44, 1123 (2008)].
A. V. Karchava, M. A. Yurovskaya, T. R. Wagner, B. L. Zybailov, and Y. G. Bundel, Tetrahedron: Asymmetry, 6, 2895 (1995).
L. W. Covert and H. Adkins, J. Am. Chem. Soc., 54, 4116 (1932).
M. Botta, F. De Angelis, and R. Nicoletti, J. Heterocycl. Chem., 16, 501 (1979).
A. M. Cuardo, M. P. Matia, J. L. Garsia, J. J. Vaquero, and J. Alvares-Builla, Synth. Commun., 21, 535 (1991).
M.-L. Bennasar, E. Zulaica, B. A. Sufi, and J. Bosch, Tetrahedron, 52, 8601 (1996).
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Dedicated to Professor V. I. Minkin on the occasion of his seventieth birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 373-385, March, 2010.
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Karchava, A.V., Shuleva, I.S., Ovcharenko, A.A. et al. 2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions. Chem Heterocycl Comp 46, 291–301 (2010). https://doi.org/10.1007/s10593-010-0504-3
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DOI: https://doi.org/10.1007/s10593-010-0504-3