Abstract
The review is focused on the application of β-formyl-β-nitroenamines, one of the push—pull alkenes, having the biased electron density as well as an electrophilic formyl group and a nucleophilic amino group in the organic synthesis. Due to the multi-functionality, β-formyl-β-nitroenamines exhibit versatile reactivity to facilitate the synthesis of polyfunctionalized compounds possessing push—pull property. Nitroenamines serve as a synthetic equivalent of unstable nitromalonaldehyde to afford nitropyrazoles, nitropyrimidines, nitrodiazepines, and nitrophenoles upon treatment with dinucleophiles such as hydrazines, amidines, 1,2-diamines, and ketones, respectively. When active methylene compounds allowed reacting with the nitroenamines, polyfunctionalized pyridones and 2-amino-5-nitropyridines are obtained. In addition, nitroenamines undergo [4+2] self-condensation to afford 3,5-dinitropyridinium ion, which is easily trapped by benzene derivatives leading to 4-arylated 1,4-dihydropyridines.
Similar content being viewed by others
References
R. G. Tasaganva, R. V. Doddamani, S. R. Inamdar, M. Y. Kariduraganavar, Optik, 2015, 126, 4991
N. Krausse, H. Butenschoen, Eur. J. Org. Chem., 2014, 6686
M. K. Lee, J. Williams, R. J. Twieg, J. Rao, W. E. Moerner, Chem. Sci., 2013, 4, 220
I. Kikas, B. Carlotti, I. Skoric, M. Sindler-Kulyk, U. Mazzucato, A. Spalletti, J. Photochem. Photobiol., A, 2012, 244, 38
A. Bolduc, Y. Dong, A. Guerin, W. G. Skene, Phys. Chem. Chem. Phys., 2012, 14, 6946
J. He, S. M. Mathew, S. D. Cornett, S. C. Grundy, C. S. Hartley, Org. Biomol. Chem., 2012, 10, 3398
J. Rotzler, D. Vonlanthen, A. Barsella, A. Boeglin, A. Fort, M. Mayor, Eur. J. Org. Chem., 2009, 1241
M. Ronchi, M. Pizzotti, A. Orbelli Biroli, S. Righetto, R. Ugo, P. Mussini, M. Cavazzini, E. Lucenti, M. Salsa, P. Fantucci, J. Phys. Chem. C, 2009, 113, 2745.
N. Nishiwaki, Y. Tohda, M. Ariga, Bull. Chem. Soc. Jpn., 1996, 69, 1997.
C. Shimokawa, S. Yokota, Y. Tachi, N. Nishiwaki, M. Ariga, S. Itoh, Inorg. Chem., 2003, 42, 8395.
N. Nishiwaki, S. Hirao, J. Sawayama, K. Saigo, Heterocycles, 2012, 84, 115.
P. E. Fanta, R. A. Stein, Chem. Rev., 1960, 60, 261.
P. E. Fanta, Org. Synth., Coll. Vol. 4, Wiley, New York, 1963, p. 844.
N. Nishiwaki, T. Ogihara, T. Takami, M. Tamura, M. Ariga, J. Org. Chem., 2004, 69, 8382.
A. L. Satz, T. C. Bruice, Acc. Chem. Res., 2002, 35, 86.
H. J. Anderson, Can. J. Chem., 1959, 37, 2053
A. Treibs, H. G. Kolm, Justus Liebigs Ann. Chem., 1958, 577, 176
H. Fischer, W. Zerweck, Z. Kenntnis, Chem. Ber., 1922, 55, 1954.
Y. Nakaike, Y. Kamijo, S. Mori, M. Tamura, N. Nishiwaki, M. Ariga, J. Org. Chem., 2005, 70, 10169.
Y. Nakaike, D. Hayashi, N. Nishiwaki, Y. Tobe, M. Ariga, Org. Biomol. Chem., 2009, 7, 325.
Y. Nakaike, N. Taba, S. Itoh, Y. Tobe, N. Nishiwaki, M. Ariga, Bull. Chem. Soc. Jpn., 2007, 80, 2413.
O. N. Chupakhin, V. L. Rusinov, A. A. Tumashov, E. O. Sidorov, I. V. Karpin, Tetrahedron Lett., 1992, 33, 3695
M. Wahren, Z. Chem., 1969, 9, 241
D. J. Brown, J. S. Harper, J. Chem. Soc., 1965, 5542
M. Wahren, Z. Chem., 1966, 6, 181.
G. Kaupp, M. R. Naimi-Jamal, J. Schmeyers, Tetrahedron, 2003, 59, 3753
D. F. Perepichka, M. R. Bryce, A. S. Batsanov, E. J. L. McInnes, J. P. Zhao, R. D. Farley, Chem. Eur. J., 2002, 8, 4656
A. J. Fatiadi, Synthesis, 1978, 165
A. J. Fatiadi, Synthesis, 1978, 241.
Y. Nakaike, N. Nishiwaki, M. Ariga, Y. Tobe, J. Org. Chem., 2014, 79, 2163.
M.-L. Bennasar, T. Roca, M. Monerris, C. Juan, J. Bosch, Tetrahedron, 2002, 58, 8099
S. Yamada, T. Minoso, M. Ichikawa, C. Morita, Tetrahedron, 2001, 57, 8939
M.-L. Bennasar, B. Vidal, J. Bosch, J. Org. Chem., 1995, 60, 4280
R. Yamaguchi, Y. Nakazono, T. Matsuki, E. Hata, M. Kawanishi, Bull. Chem. Soc. Jpn., 1987, 60, 215
R. Yamaguchi, M. Moriyasu, M. Yoshioka, M. Kawanisi, J. Org. Chem., 1985, 50, 287.
I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley-Intersci., London, 1976, p. 34–85
Y. Ishihara, T. Tanaka, G. Goto, J. Chem. Soc., Perkin Trans. 1, 1992, 3401.
S. G. A. Moinuddin, B. Youn, D. L. Bedgar, M. A. Costa, G. L. Helms, C. Kang, L. B. Davin, N. G. Lewis, Org. Biomol. Chem., 2006, 4, 808
S. Nakano, W. Sakane, H. Oinaka, Y. Fujimoto, Bioorg. Med. Chem., 2006, 14, 6404
C. R. Pudney, S. Hay, M. J. Sutcliffe, N. S. Scrutton, J. Am. Chem. Soc., 2006, 128, 14053.
H. Asahara, M. Hamada, Y. Nakaike, N. Nishiwaki, RSC Adv., 2015, 5, 90778.
S. Lee, S. Diab, P. Queval, M. Sebban, I. Chataigner. S. R. Piettre, Chem.–Eur. J., 2013, 19, 7181.
J. Šturala, S. Boháčová, J. Chudoba, R. Metelková, R. Cibulka, J. Org. Chem., 2015, 80, 2676
M. Winkler, B. Cakir, W. Sander, J. Am. Chem. Soc., 2004, 126, 6135
E. Plazek, Recl. Trav. Chim. Pays-Bas, 1953, 72, 569.
G. P. Sagitullina, L. V. Glizdinskaya, R. S. Sagitullin, Chem. Heterocycl. Compd. (Engl. Transl.), 2005, 41, 739 [Khim. Geterotsikl. Soedin., 2005, 858].
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2129—2142, September, 2016.
Rights and permissions
About this article
Cite this article
Nakaike, Y., Asahara, H. & Nishiwaki, N. Construction of push—pull systems using β-formyl-β-nitroenamine. Russ Chem Bull 65, 2129–2142 (2016). https://doi.org/10.1007/s11172-016-1561-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-016-1561-2