Abstract
The reaction of benzaldehyde, α-nitro ketone, and cyanothioacetamide in the presence of morpholine has given the novel 3,4-trans-2-R-5-cyano-2-hydroxy-3-nitro-4-phenyl-1,2,3,4-tetrahydropyridine-6-thiolates. It was found that the reaction occurs via the formation of 1-amino-2-cyano-4-nitro-5-oxo-3-phenyl-1,2-pentene-1-thiolate. In the case of α-nitroacetophenone, 3,4-trans-4,5-trans-5-cyano-2-hydroxy-3-nitro-2,4-diphenylhexahydropyridine-6(1H)-thione was also obtained. The use of α-nitroesters in place of the nitro ketones in the reaction leads to morpholinium 2-aryl-1-carbethoxy-3-cyano-1-nitro-3-thiocarbamoylpropyl-1-ates as the single product.
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REFERENCES
V. P. Litvinov, L. A. Rodinovskaya, Yu. A. Sharanin, A. M. Shestopalov, and A. Senning, Sulfur Reports, 13, 1 (1992).
G. A. Shveikhgeimer, Khim. Geterotsikl. Soedin., 1299 (1994).
A. M. Shestopalov, V. P. Litvinov, L. A. Rodinovskaha, and Yu. A. Sharanin, Synthesis, 402 (1991).
A. M. Shestopalov, Yu. A. Sharanin, L. A. Rodinovskaya, and V. P. Litvinov, Zh. Org. Khim., 26, 1588 (1990).
A. M. Shestopalov, O. P. Bogomolova, L. A. Rodinovskaya, V. P. Litvinov, B. Bujnicki, M. Mikholajczyk, V. N. Nesterov, and Yu. T. Struchkov, Heteroatom Chem., 4, 593 (1993).
A. M. Shestopalov, L. A. Rodinovskaya, Yu. A. Sharanin, and V. P. Litvinov, Izv. Akad. Nauk SSSR. Ser. Khim., 2593 (1990).
H. Gunther, Introduction to a Course in NMR spectroscopy /Russian translation/, Mir, Moscow (1984) p. 129.
V. M. Potapov, Stereochemistry, Khimiya, Moscow (1976).
A. A. Krauze, E. E. Liepin'sh, Yu. E. Pelcher, Z. A. Kalme, I. V. Dipan, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., 95 (1985).
V. N. Nesterov, V. E. Shklover, Yu. T. Struchkov, Yu. A. Sharanin, A. M. Shestopalov, and L. A. Rodinovskaya, Acta Crystallogr., C41, 1191 (1985).
R. J. Coombes, in: D. H. R. Barton and W. D. Ollis (eds.), Comprehensive Organic chemistry [in Russian], Khimiya, Moscow (1982), Vol. 3, p. 412.
V. P. Litvinov, V. K. Promonenkov, Yu. A. Sharanin, A. M. Shestopalov, L. A. Podinovskaha, V. Yu. Mortikov, and V. S. Bogdanov, Izv. Akad. Nauk SSSR. Ser. Khim., 2101 (1985).
Yu. A. Sharanin, A. M. Shestopalov, L. A. Rodinovskaya, V. N. Nesterov, V. E. Shklover, Yu. T. Struchkov, V. K. Promonenkov, and V. P. Litvinov, Zh. Org. Khim., 22, 2600 (1986).
J. G. Burr, in The Chemistry of the Nitro and Nitroso Groups, Vol. 1, Mir, Moscow (1972), p. 406.
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Rodinovskaya, L.A., Chunikhin, K.S. & Shestopalov, A.M. Study of the Three-component Reaction of α-Nitrocarbonyl Compounds, Aromatic Aldehydes, and Cyanothioacetamide. Chemistry of Heterocyclic Compounds 38, 442–448 (2002). https://doi.org/10.1023/A:1016035406623
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DOI: https://doi.org/10.1023/A:1016035406623