The reaction of (2E,6E)-bis(chloromethylidene)thiomorpholin-4-amine and -selenomorpholin-4-amine with propionaldehyde, benzaldehyde, or 4-pyridinecarbaldehyde in benzene in the presence of catalytic amounts of formic acid gave the corresponding hydrazones, the N-(organylmethylidene)-(2E,6E)bis-(chloromethylidene)thiomorpholin-4-amines and -selenomorpholin-4-amines, as trans isomers. The structure of the hydrazones was confirmed by 1H and 13C NMR, as well as 2D 1H–1H NOESY experiments.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. N. Suvarapu, Y. K. Seo, S. O. Baek, and V. R. Ammireddy, E-J. Chem., 9, 1288 (2012).
S. Rollas and Ş. G. Küçükgüzel, Molecules, 12, 1910 (2007).
W. W. Wardakhan and E. M. Samir, J. Chil. Chem. Soc., 57, 1118 (2012).
A. Petitjean, R. G. Khoury, N. Kyritsakas, and J.-M. Lehn, J. Am. Chem. Soc., 126, 6637 (2004).
S. Ulrich, A. Petitjean, and J.-M. Lehn, Eur. J. Inorg. Chem., 1913 (2010).
X. Su, T. Lessing and I. Aprahamian, Beilstein J. Org. Chem., 8, 872 (2012).
S. C. Burdette, Nat. Chem., 4, 695 (2012).
S. M. Landge, E. Tkatchouk, D. Benítez, D. A. Lanfranchi, M. Elhabiri, W. A. Goddard, III, and I. Aprahamian, J. Am. Chem. Soc., 133, 9812 (2011).
D. Ray, J. T. Foy, R. P. Hughes, and I. Aprahamian, Nat. Chem., 4, 757 (2012).
A.-M. Stadler, J. Ramírez, and J.-M. Lehn, Chem.–Eur. J., 16, 5369 (2010).
A. V. Martynov, N. A. Makhaeva, L. I. Larina, and S. V. Amosova, Khim. Geterotsikl. Soedin., 1526 (2012). [Chem. Heterocycl. Compd., 48, 1425 (2012)].
L. B. Krivdin, L. I. Larina, K. A. Chernyshev, and A. Yu. Rulev, Magn. Reson. Chem., 44, 178 (2006).
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 34.
J. P. Verge and P. Roffey, J. Med. Chem., 18, 794 (1975).
M. C. Neville and J. P. Verge, J. Med. Chem., 20, 946 (1977).
W. J. Ross and W. B. Jamieson, J. Med. Chem., 18, 158 (1975).
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 385.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 852–856, May, 2013.
Rights and permissions
About this article
Cite this article
Martynov, A.V., Makhaeva, N.A. & Amosova, S.V. N-(Organylmethylidene)bis(chloromethylidene)thiomorpholin-4-amines and -selenomorpholin-4-amines. Chem Heterocycl Comp 49, 797–801 (2013). https://doi.org/10.1007/s10593-013-1311-4
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1311-4