Data on the reactions of unsaturated nitro compounds with aromatic and heteroaromatic compounds over the last 65 years and also their reactions under the conditions of asymmetric catalysis are examined and summarized.
Similar content being viewed by others
References
J. L. Vicario, D. Badía, and L. Carillo, Synthesis, 2065 (2007).
C. F. Nising and S. Bräse, Chem. Soc. Rev., 37, 1218 (2008).
D. Enders, K. Lüttgen, and A. A. Narine, Synthesis, 959 (2007).
D. Enders, A. Saint-Dizier, M.-I. Lannou, and A. Lenzen, Eur. J. Org. Chem., 29 (2006).
F. Palacios, C. Alonso, and J. M. de los Santos, Chem. Rev., 105, 899 (2005).
S. Kurokava and A. G. Anderson, Jr., Bull. Chem. Soc. Jpn., 58, 367 (1985).
W. E. Noland and P. J. Hartman, J. Am. Chem. Soc., 76, 3227 (1954).
D. Ranganathan, C. B. Rao, S. Ranganathan, A. K. Mehrotra, and R. Iyengar, J. Org. Chem., 45, 1185 (1980).
T. Ooi, S. Takada, K. Doda, and K. Maruoka, Angew. Chem., Int. Ed., 45, 7606 (2006).
W. E. Noland, G. M. Christensen, G. L. Sauer, and G. G. S. Dutton, J. Am. Chem. Soc., 77, 456 (1955).
G. Dupeyre, P. Lemoine, N. Ainseba, S. Michel, and X. Cachet, Org. Biomol. Chem., 9, 7780 (2011).
W. E. Noland and R. A. Hovden, J. Org.Chem., 24, 894 (1959).
P. M. Habib, V. Kavala, C. Kuo, and C. Yao, Tetrahedron Lett., 49, 7005 (2008).
H. Firouzabadi, N. Iranpoor, and F. Nowrouzi, Chem. Commun., 789 (2005).
A. Z. Halimehjani, F. Aryanasab, and M. R. Saidi, Tetrahedron Lett., 50, 1441 (2009).
D. K Barange, V. Kavala, B. Rama Raju, C.-W. Kuo, C. Tseng, Y.-C. Tu, and C.-F. Yao, Tetrahedron Lett., 50, 5116 (2009).
T. Ohta, K. Shudo, and T. Okamoto, Tetrahedron Lett., 25, 325 (1984).
K. Shudo, T. Ohta, and T. Okamoto, J. Am. Chem. Soc., 103, 645 (1981).
K. Okabe, T. Ohwada, T. Ohta, and K. Shudo, J. Org. Chem., 54, 733 (1989).
T. Ohwada, T. Ohta, and K. Shudo, Tetrahedron, 43, 297 (1987).
T. Ohwada, A. Itai, T. Ohta, and K. Shudo, J. Am. Chem. Soc., 109, 7036 (1987).
R. Ballini and M. Petrini, Tetrahedron, 60, 1017 (2004).
W. E. Noland, Chem. Rev., 55, 137 (1955).
D. E. Seebach, W. Colvin, F. Lehr, R. Weller, and M. T. Ballini, Chimia, 33, 1 (1979).
E. E. van Tamelen and R. J. Thiede, J. Am. Chem. Soc., 74, 2615 (1952).
M. F. Hawthorne, J. Am. Chem. Soc., 79, 2510 (1957).
S. F. Sun and J. T. Folliard, Tetrahedron, 27, 323 (1971).
H. Feuer and A. T. Nielsen, J. Am. Chem. Soc., 84, 688 (1962)
T. Ohwada, K. Okabe, T. Ohta, and K. Shudo, Tetrahedron, 46, 7539 (1990).
J.-M. Coustard, Tetrahedron, 51, 10929 (1995).
J.-М. Coustard, Tetrahedron, 55, 5809 (1999).
J.-M. Coustard, Tetrahedron, 52, 9509 (1996).
Y. Soro, F. Bamba, S. Siaka, and J.-M. Coustard, Tetrahedron Lett., 47, 3315 (2006).
J.-M. Coustard, Y. Soro, S. Siaka, F. Bamba, and A. Cousson, Tetrahedron, 62, 3320 (2006).
J. Guillaumel, P. Demerseman, J.-М. Clavel, and R. Royer, Tetrahedron, 36, 2459 (1980).
P. Demerseman, J. Guillaumel, J.-М. Clavel, and R. Royer, Tetrahedron Lett., 19, 2011 (1978).
J. Guillaumel, P. Demerseman, J.-М. Clavel, and R. Royer, J. Heterocycl. Chem., 17, 1531 (1980).
B. Lantaňo, J. M. Aguirre, E. A. Ugliarolo, R. Torviso, N. Pomilio, and G. Y. Moltrasio, Tetrahedron, 68, 913 (2012).
A. Lambert, J. D. Rose, and B. C. L. Weedon, J. Chem. Soc., 42 (1949).
C. D. Hurd, M. E. Nilson, and D. M. Wikholm, J. Am. Chem. Soc., 72, 4697 (1950).
Z. Tu, В. Rama Raju, T.-R. Liou, V. Kavala, C.-W. Kuo, Y. Jang, Y.-H. Shih, C.-C. Wang, and C.-F. Yao, Tetrahedron, 65, 2436 (2009).
K. Lee and D. Y. Oh, Tetrahedron Lett., 29, 2977 (1988).
M. M. Alam, R. Varala, and S. R. Adapa, Tetrahedron Lett., 44, 5115 (2003).
J. S. Yadav, B. V. S. Reddy, G. Baishya, K. V. Reddy, and A. V. Narsaiah, Tetrahedron, 61, 9541 (2005).
K. Manabe, N. Aoyama, and S. Kobayashi, Adv. Synth. Catal., 343, 174 (2001).
I. Komoto and S. Kobayashi, Org. Lett., 4, 1115 (2002).
J. S. Yadav, S. Abraham, B. V. S. Raddy, and G. Sabitha, Synthesis, 2165 (2001).
Z.-P. Zhan, R.-F. Yang, and K. Lang, Tetrahedron Lett., 46, 3859 (2005).
M. Bandini, P. G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva, and A. Umani-Ronchi, J. Org. Chem., 67, 3700 (2002).
M. Bandini, P. Melchiorre, and A. Umani-Ronchi, Synthesis, 1110 (2002).
N. Azizi, F. Arynasab, and M. R. Saidi, Org. Biomol. Chem., 4, 4275 (2006).
A. Z. Halimehjani, M. V. Farvardin, H. P. Zanussi, M. A. Ranjbari, and M. Fattahi, J. Mol. Catal. A: Chem., 381, 21 (2014).
R. Murugan, M. Karthikeyan, P. T. Perumal, and B. S. R. Reddy, Tetrahedron, 61, 12275 (2005).
G. Bartoli, M. Bosco, S. Giuli, A. Giuliani, L. Lucarelli, E. Marcantoni, L. Sambri, and E. Torregiani, J. Org. Chem., 70, 1941 (2005).
G. Bartoli, E. Marcantoni, and L. Sambri, Synlett, 2101 (2003).
N. N. Wan, Y. L. Yang, W. P. Wang, Z. F. Xie, and J. D. Wang, Chin. Chem. Lett., 22, 1155 (2011).
G. Huang, H. Sun, X. Qiu, Y. Shen, J. Jiang, and L. Wang, J. Organomet. Chem., 696, 2949 (2011).
Z. Liu, T. Zhang, and M. Shi, Organometallics, 27, 2668 (2008).
L. Bianci, G. Giorgi, M. Maccagno, G. Petrillo, G. Scapolla, and C. Tavani, Tetrahedron Lett., 53, 752 (2012).
C. Praveen, K. Karthikeyan, and P. T. Perumal, Tetrahedron, 65, 9244 (2009).
C. Lin, J. Hsu, M. N. V. Sastry, H. Fang, Z. Tu, J.-T. Liu, and Y. Ching-Fa, Tetrahedron, 61, 11751 (2005).
B. K. Banik, M. Fernandez, and C. Alvarez, Tetrahedron Lett., 46, 2479 (2005).
G. L. Wu and L. M. Wu, Chin. Chem. Lett., 19, 55 (2008).
R. P. Herrera, V. Sgarzani, L. Bernardi, and A. Ricci, Angew. Chem., Int. Ed., 44, 6576 (2005).
M. Ganesh and D. Seidel, J. Am. Chem. Soc., 130, 16464 (2008).
E. M. Fleming, T. McCabe, and S. J. Connon, Tetrahedron Lett., 47, 7037 (2006).
T.-Y. Liu, H.-L. Cui, Q. Chai, J. Long, B.-J. Li, Y. Wu, L.-S. Ding, and Y.-C. Chen, Chem. Commun., 2228 (2007).
D. M. Heinrich, J.-J. Youte, W. A. Denny, and M. Tercel, Tetrahedron Lett., 52, 7000 (2011).
T. R Kelly and M. H. Kim, J. Am. Chem. Soc., 116, 7072 (1994).
M. C. Etter, Z. Urbañczyk-Lipkowska, M. Zia-Ebrahimi, and T. W. Panunto, J. Am. Chem. Soc., 112, 8415 (1990).
W. Zhuang, R. G. Hazell, and K. A. Jørgensen, Org. Biomol. Chem., 3, 2566 (2005).
A. K. Ghosh, P. Mathivanan, and J. Cappiello, Tetrahedron: Asymmetry, 9, 1 (1998).
Y.-X. Lia, S.-F. Zhu, Y. Yang, and Q.-L. Zhou, J. Org. Chem., 71, 75 (2006).
Y. Sui, L. Liu, J.-L. Zhao, D. Wang, and Y.-J. Chen, Tetrahedron, 63, 5173 (2007).
P. K. Singh, A. Bisai, and V. K. Singh, Tetrahedron Lett., 48, 1127 (2007).
S. Lin and T. You, Tetrahedron, 65, 1010 (2009).
S.-F. Lu, D.-M. Du, and J. Xu, Org. Lett., 8, 2115 (2006).
S. McKeon, H. Müller-Bunz, and P. J. Guiry, Eur. J. Org. Chem., 4833 (2009).
H. Liu, S.-F. Lu, J. Xu, and D.-M. Du, Chem. Asian J., 3, 1111 (2008).
H. Liu, J. Xu, and D.-М. Du, Org. Lett., 9, 4725 (2007).
H. Lin and D.-М. Du, Eur. J. Org. Chem., 2121 (2010).
E. Guiu, C. Claver, J. Benet-Buchholz, and S. Castillόn, Tetrahedron: Asymmetry, 15, 3365 (2004).
N. Arai, N. Yokoyama, and A. Yanagisawa, Chem.-Eur. J., 14, 2052 (2008).
T. Arai and N. Yokoyama, Angew. Chem., Int. Edit., 47, 4989 (2008).
N. Yokoyama and T. Arai, Chem. Commun., 3285 (2009).
H. Liu and D.-М. Du, Adv. Synth. Catal., 352, 1113 (2010).
H. Y. Kim, S. Kim, and K. Oh, Angew. Chem., Int. Ed., 49, 4476 (2010).
Z.-L. Yuan, Z.-Y. Lei, and M. Shi, Tetrahedron: Asymmetry, 19, 1339 (2008).
F. Guo, G. Lai, S. Xiong, S. Wang, and Z. Wang, Chem. – Eur. J., 16, 6438 (2010).
M. Bandini, A. Garelli, M. Rovinetti, S. Tommasi, and A. Umani-Ronchi, Chirality, 17, 522 (2005).
D. Carmona, M. P. Lamata, A. Sánchez, F. Viguri, and L. A. Oro, Tetrahedron: Asymmetry, 22, 893 (2011).
J. Iton, K. Fuchibe, and T. Akiyama, Angew. Chem., Int. Ed., 47, 4016 (2008).
T. Hirata and M. Yamanaka, Chem. Asian J., 6, 510 (2011).
J.-H. Lin and J.-C. Xiao, Eur. J. Org. Chem., 4536 (2011).
Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, and S.-L. You, Chem. – Eur. J., 15, 3351 (2009).
C. Zheng, Y.-F. Sheng, Y.-X. Li, and S.-L. You, Tetrahedron, 66, 2875 (2010).
The work was carried out with support from the Russian Foundation for Basic Research (grants 13-03-003004а and 14-03-31288mol_a).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 648-673, May, 2014.
Rights and permissions
About this article
Cite this article
Smirnov, A.N., Aksenov, N.A., Malikova, I.V. et al. Arenes and Hetarenes in Reactions with unsaturated Nitro Compounds (Review). Chem Heterocycl Comp 50, 594–618 (2014). https://doi.org/10.1007/s10593-014-1514-3
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1514-3