The reaction of Mannich bases derived from 2-naphthol with 4-(2-nitrovinyl)morpholine or N,N-di-methyl(2-nitrovinyl)amine in acetic anhydride gives 2-nitro-1H-benzo[f]chromenes. This reaction may be regarded formally as the addition of a push-pull olefin acting as a 1,2-ambiphile with naphthalenic o-quinone methide acting as a 1,4-ambiphilic reagent.
Similar content being viewed by others
References
D. Lloyd and H. McNab, Angew. Chem. Int. Ed. Engl., 15, 459 (1976).
E. V. Babaev, Chem. Heterocycl. Comp., 29, 796 (1993) [Khim. Geterotsikl. Soedin., 937 (1993)].
Z. He, A. Zajdlik, and A. K. Yudin, Acc. Chem. Res., 47, 1029 (2014).
V. A. Osyanin, E. A. Ivleva, and Yu. N. Klimochkin, Synth. Commun., 42, 1832 (2012).
L. René, Synthesis, 69 (1989).
V. A. Osyanin, D. V. Osipov, M. R. Demidov, and Yu. N. Klimochkin, J. Org. Chem., 79, 1192 (2014).
V. A. Osyanin, D. V. Osipov, and Yu. N. Klimochkin, J. Org. Chem., 78, 5505 (2013).
T. B. Samarakoon, M. Y. Hur, R. D. Kurtz, and P. R. Hanson, Org. Lett., 12, 2182 (2010).
D. V. Osipov, V. A. Osyanin, and Yu. N. Klimochkin, Russ. J. Org. Chem., 49, 398 (2013) [Zh. Org. Khim., 49, 412 (2013)].
J. B. Littman and W. R. Bode, J. Am. Chem. Soc., 52, 1655 (1930).
H. R. Snyder and J. H. Brewster, J. Am. Chem. Soc., 70, 4230 (1948).
W. R. Brode and J. B. Littman, J. Am. Chem. Soc., 53, 1531 (1931).
M. Faulques, L. René, and R. Royer, Synthesis, 260 (1982).
T. Severin and R. Brück, Chem. Ber., 98, 3847 (1965).
This work was carried out with the financial support from the Ministry of Education and Science of the Russian Federation within the framework of the baseline of the State Assignment for scientific activity No. 2014/199 using the scientific equipment at the Samara State Technical University Collective Use Center "Physicochemical Investigation of Substances and Materials"
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1663–1668, November, 2014.
Rights and permissions
About this article
Cite this article
Osyanin, V.A., Lukashenko, A.V., Osipov, D.V. et al. Synthesis of 2-Nitro-1H-Benzo[f]Chromenes. Chem Heterocycl Comp 50, 1528–1533 (2015). https://doi.org/10.1007/s10593-014-1620-2
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1620-2