Abstract
Methods for the design of nitrogen-containing heterocyclic systems involving the formation of C-N bonds under the conditions of the Mitsunobu reaction are discussed.
Similar content being viewed by others
References
O. Mitsunobu, Synthesis, 1 (1981).
B. R. Castro, Org. React., 29, 1 (1983).
D. L. Hughes, Org. React., 42, 335 (1993).
D. L. Hughes, Org. Prep. Proced. Int., 28, 127 (1996).
O. Mitsunobu, M. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 40, 935 (1967).
S. Csaba, H. Sandor, and M. Sandor, J. Heterocycl. Chem., 34, 349 (1997).
S. Dandapani and D. P. Curran, Chem. Eur. J., 10, 3130 (2004).
M. Varasi, K. A. M. Walker, and M. L. Maddox, J. Org. Chem., 52, 4235 (1987).
C. Ahn, R. Correia, and P. DeShong, J. Org. Chem., 67, 1751 (2002).
S. Schenk, J. Weston, and E. Anders, J. Am. Chem. Soc, 127, 12566 (2005).
C. Bournaud, M. Bonin, and L. Micouin, Org. Lett., 8, 3041 (2006).
T. Tsunoda and T. Yamamia, Tetrahedron Lett., 34, 1639 (1993).
T. Tsunoda, K. Uemoto, T. Ohtani, H. Kaku, and S. Itô, Tetrahedron Lett., 40, 7359 (1999).
S. Itô and T. Tsunoda, Pure Appl. Chem., 71, 1053 (1999).
E. A. Véliz, P. A. Beal, Tetrahedron Lett., 47, 3153 (2006).
J. L. Castro, V. G. Matassa, J. Org. Chem., 59, 2289 (1994).
D. J. Cane-Honeysett, M. D. Dowle, and M. E. Wood, Tetrahedron, 61, 2141 (2005).
M. E. Wood, D. J. Cane-Honeysett, and M. D. Dowle, J. Chem. Soc, Perkin Trans. 1, 2046 (2002).
B. H. Lipshutz, D. W. Chung, B. Rich, and R. Corral, Org. Lett., 8, 5069 (2006).
A. Bombrun and G. Casi, Tetrahedron Lett., 43, 2187 (2002).
T. Tsunoda, F. Ozaki, N. Shirakata, Y. Tamaoka, H. Yamamoto, and S. Itô, Tetrahedron Lett., 37, 2463 (1996).
U. M. Lindström and P. Somfai, Synthesis, 109 (1998).
H. Ohno, A. Toda, Y. Takemoto, N. Fujii, and T. Ibuka, J. Chem. Soc., Perkin Trans. 1, 2949 (1999).
A. L. Braga, P. Milani, M. W. Paixão, G. Zeni, O. E. D. Rodrigues, and E. F. Alves, Chem. Commun., 2488 (2004).
S. G. Petersen and S. R. Rajski, J. Org. Chem., 70, 5833 (2005).
J. J. Turner, M. A. Leeuwenburgh, G. A. van der Marel, and J. H. van Boom, Tetrahedron Lett., 42, 8713 (2001).
J. J. Turner, F. D. Sikkema, D. V. Filippov, G. A. van der Marel, and J. H. van Boom, Synlett, 1727 (2001).
W. J. Moran, K. M. Goodenough, P. Raubo, and J. P. A. Harrity, Org. Lett., 5, 3427 (2003).
J. A. Joule and K. Mills, Heterocyclic Chemistry, Blackwell Science Ltd., Oxford (2000), p. 536.
A. Bisai and V. K. Singh, Tetrahedron Lett., 48, 1907 (2007).
S. Quader, S. E. Boyd, I. D. Jenkins, and T. A. Houston, J. Org. Chem., 72, 1962 (2007).
A. H. Linares, D. Fourmy, J.-L. Fourrey, and A. Loukaci, Synthetic Commun., 36, 487 (2006).
M. G. Stocksdale, S. Ramurthy, and M. J. Miller, J. Org. Chem., 63, 1221 (1998).
J. R. Bellettini and M. J. Miller, Tetrahedron Lett., 38, 167 (1997).
M. M. Meloni and M. Taddei, Org. Lett., 3, 337 (2001).
C. T. Brain, A. Chen, A. Nelson, N. Tanikkul, and E. J. Thomas, Tetrahedron Lett., 42, 1247 (2001).
H. Bittermann and P. Gmeiner, J. Org. Chem., 71, 97 (2006).
W. P. Malachowski, C. Tie, K. Wang, and R. L. Broadrup, J. Org. Chem., 67, 8962 (2002).
R. L. Broadrup, B. Wang, and W. P. Malachowski, Tetrahedron, 61, 10277 (2005).
B. A. B. Prasad, A. Bisai, and V. K. Singh, Org. Lett., 6, 4829 (2004).
D. Enders, J. Gries, and Z.-S. Kim, Eur. J. Org. Chem., 4471 (2004).
I. M. Bell, D. C. Beshore, S. N. Gallicchio, and T. M. Williams, Tetrahedron Lett., 41, 1141(2000).
J. C. Pelletier, J. Rogers, J. Wrobel, M. C. Perez, and E. S. Shen, Bioorg. Med. Chem., 13, 5986 (2005).
P. S. Hadfield, R. H. B. Galt, Y. Sawyer, N. J. Layland, and M. I. Page, J. Chem. Soc., Perkin Trans. 1, 503 (1997).
J. Van Betsbrugge, D. Tourwé, B. Kaptein, H. Kierkels, and R. Broxterman, Tetrahedron, 53, 9233 (1997).
M. K. Pandey, A. Bisai, A. Pandey, and V. K. Singh, Tetrahedron Lett., 46, 5039 (2005).
V. Kumar and N. G. Ramesh, Tetrahedron, 62, 1877 (2006).
S. P. Moore, S. C. Coote, P. O’Brein, and J. Gilday, Org. Lett., 8, 5145 (2006).
W.-C. Haase and K. H. Dötz, Tetrahedron Lett., 40, 2919 (1999).
W.-C. Haase, M. Nieger, and K. H. Dötz, Chem. Eur. J., 5, 2014 (1999).
H. S. Jeon, J. H. Yoo, J. N. Kim, and T. H. Kim, Tetrahedron Lett, 48, 439 (2007).
E. Erba, D. Pocar, and P. Trimarco, Synthesis, 2693 (2006).
D. Font, A. Linden, M. Heras, and J. M. Villalgordo, Tetrahedron, 62, 1433 (2006).
S. B. Mhaske and N. P. Argade, J. Org. Chem., 69, 4563 (2004).
D. Ma and J. Zhang, J. Chem. Soc., Perkin Trans. 1, 1703 (1999).
K. G. Poullennec and D. Romo, J. Am. Chem. Soc., 125, 6344 (2003).
D. A. Bianchi and T. S. Kaufman, Can. J. Chem., 78, 1165 (2000).
S. B. Kang, E. J. Ahn, Y. Kim, and Y. H. Kim, Tetrahedron Lett., 37, 9317 (1996).
N. Langlois and O. Calvez, Tetrahedron Lett., 41, 8285 (2000).
H. Mao, G. J. Joly, K. Peeters, G. J. Hoornaert, and F. Compernolle, Tetrahedron, 57, 6955 (2001).
R. Grandel and U. Kazmaier, Tetrahedron Lett., 38, 8009 (1997).
T. J. Greshock and R. L. Funk, Org. Lett., 3, 3511 (2001).
L. Sun, P. Li, N. Amankulor, W. Tang, D. W. Landry, and K. Zhao, J. Org. Chem., 63, 6472 (1998).
Y. Aoyagi, Y. Saitoh, T. Ueno, M. Horiguchi, and K. Takeya, J. Org. Chem., 68, 6899 (2003).
S. A. Weissman, S. Lewis, D. Askin, R. P. Volante, and P. J. Reider, Tetrahedron Lett., 39, 7459 (1998).
C. A. Olsen, C. Christensen, B. Nielsen, F. M. Mohamed, M. Witt, R. P. Clausen, J. L. Kristensen, H. Franzyk, and J. W. Jaroszewski, Org. Lett., 8, 3371 (2006).
C. W. Zapf, J. R. Del Valle, and M. Goodman, Bioorg. Med. Chem. Lett., 15, 4033 (2005).
P. Arya, C.-Q. Wei, M. L. Barnes, and M. Daroszewska, J. Comb. Chem., 6, 65 (2004).
P.-P. Kung and E. Swayze, Tetrahedron Lett., 40, 5651 (1999).
E. E. Swayze, Tetrahedron Lett., 38, 8643 (1997).
T. Kan and T. Fukuyama, Chem. Commun., 353 (2004).
T. Ishiwata, T. Hino, H. Koshino, Y. Hashimoto, T. Nakata, and K. Nagasawa, Org. Lett., 4, 2921 (2002).
A. Dondoni, B. Richichi, A. Marra, and D. Perrone, Synlett, 1711 (2004).
D. M. Goldstein and P. Wipf, Tetrahedron Lett., 37, 739 (1996).
L. R. Lampariello, D. Piras, M. Rodriquez, and M. Taddei, J. Org. Chem., 68, 7893 (2003).
A. Nouvet, F. Lamaty, and R. Lazaro, Tetrahedron Lett., 39, 2099 (1998).
A. Nouvet, M. Binard, F. Lamaty, J. Martinez, and R. Lazaro, Tetrahedron, 55, 4685 (1999).
P. Ribière, V. Declerck, J. Martinez, and F. Lamaty, Chem. Rev., 106, 2249 (2006).
J. K. Mishra and G. Panda, J. Comb. Chem., 9, 321 (2007).
L. Banfi, A. Basso, G. Guanti, N. Kielland, C. Repetto, and R. Riva, J. Org. Chem., 72, 2151 (2007).
D. Pappo and Y. Kashman, Tetrahedron, 59, 6493 (2003).
T. Kan, A. Fujiwara, H. Kobayashi, and T. Fukuyama, Tetrahedron, 58, 6267 (2002).
T. Kan, H. Kobayashi, and T. Fukuyama, Synlett, 697 (2002).
A. Fujiwara, T. Kan, and T. Fukuyama, Synlett, 1667 (2000).
W. Kurosawa, T. Kan, and T. Fukuyama, J. Am. Chem. Soc., 125, 8112 (2003).
P. Ducept, D. A. Gubler, and R. M. Williams, Heterocycles, 67, 597 (2006).
M. Suzuki, M. Kambe, H. Tokuyama, and T. Fukuyama, J. Org. Chem., 69, 2831 (2004).
K. Tomooka, M. Suzuki, M. Shimada, S. Yanagitsuru, and K. Uehara, Org. Lett., 8, 963 (2006).
J. Hovinen and R. Sillanpää, Tetrahedron Lett., 46, 4387 (2005).
V. Kuksa, C. Marshall, S. Wardell, and P. K. T. Lin, Synthesis, 1034 (1999).
L. Raehm, D. G. Hamilton, and J. K. M. Sanders, Synlett, 1743 (2002).
J. G. Hansen, N. Feeder, D. G. Hamilton, M. J. Gunter, J. Becher, and J. K. M. Sanders, Org. Lett., 2, 449 (2000).
Author information
Authors and Affiliations
Additional information
Dedicated to Afanasi Andreevich Akhrem on his 95th birthday.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 347–385, March, 2008.
Rights and permissions
About this article
Cite this article
Golantsov, N.E., Karchava, A.V. & Yurovskaya, M.A. The Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds. The formation of heterocyclic systems (review). Chem Heterocycl Comp 44, 263–294 (2008). https://doi.org/10.1007/s10593-008-0042-4
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0042-4