Abstract
The mechanism was established for annelation ([2+4] cyclocondensation) of Schiff bases or azomethines by β-dicarbonyl and β,β′-tricarbonyl compounds in amphiprotic media. The condensation was found to be a self-catalyzed pericyclic process achieved through six-membered transition states. The key reaction intermediates are dipoles of quaternized azomethine ions and enol-anions of the β-dicarbonyl and β,β′-tricarbonyl compounds, which display 1,4-dipolarophilicity.
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References
M. von Strandtmann, M. P. Cohen, and J. Shavel, Jr., J. Org. Chem., 31, 797 (1966).
A. A. Akhrem, O. V. Gulyakevich, and A. L. Mikhal’chuk, in: Enamines in Organic Synthesis [in Russian], Urals Branch of the Russian Academy of Sciences, Yekaterinburg, (2001), p. 47.
M. von Strandtmann, C. Puchalski, and J. Shavel, Jr., J. Org. Chem., 33, 4010 (1968).
A. A. Akhrem, A. M. Moiseenkov, V. A. Krivoruchko, F. A. Lakhvich, and A. I. Poselenov, Izv. Akad. Nauk SSSR, Ser. Khim., 2078 (1972).
A. A. Akhrem, F. A. Lakhvich, L. G. Lis, and V. N. Pshenichnyi, Zh. Org. Khim., 15, 1395 (1979).
V. N. Pshenichnyi, O. F. Lakhvich, and V. A. Khripach, Vestsi Akad. Nauk Belarus SSR, Ser. Khim., No. 5, 70 (1991).
A. A. Akhrem, O. V. Gulyakevich, and A. L. Mikhal’chuk, in: V. G. Kartsev and G. A. Tolstikov (editors), Nitrogen-Containing Heterocycles and Alkaloids. The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and Alkaloids, vol. 1, Iridium Press, Moscow (2001), p. 19.
D. B. Rubinov, M. V. Budnikova, T. A. Zheldakova, and A. L. Mikhal’chuk, in: V. G. Kartsev and G. A. Tolstikov (editors), Nitrogen-Containing Heterocycles and Alkaloids. The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and Alkaloids, vol. 1, Iridium Press, Moscow (2001), p. 470.
O. V. Gulyakevich and A. L. Mikhal’chuk, Dokl. Akad. Nauk, 409, 57 (2006).
O. V. Gulyakevich, V. G. Zaitsev, and A. L. Mikhal’chuk, in: V. G. Kartsev and G. A. Tolstikov (editors), Nitrogen-Containing Heterocycles and Alkaloids. The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and Alkaloids, vol. 1, Iridium Press, Moscow (2001), p. 102.
A. L. Mikhal’chuk, O. V. Gulyakevich, Yu. V. Shklyaev, V. S. Shklyaev, and A. A. Akhrem, Khim. Geterotsikl. Soedin., 681 (1998). [Chem. Heterocycl. Comp., 34, 602 (1998)].
M. V. Budnikova, D. B. Rubinov, and A. L. Mikhal’chuk, Khim. Geterotsikl. Soedin., 1067 (2002). [Chem. Heterocycl. Comp., 38, 929 (2002)].
O. V. Gulyakevich, P. V. Kurman, and A. L. Mikhal’chuk, Zh. Obshch. Khim., 74, 870 (2004).
O. V. Gulyakevich and A. L. Mikhal’chuk, in: V. G. Kartsev (editor), Nitrogen-Containing Heterocycles and Alkaloids. The Chemistry and Biological Activity of Nitrogen-Containing Heterocycles and Alkaloids, vol. 2, ICSPF, Moscow (2006), p. 308.
O. V. Gulyakevich, P. V. Kurman, A. S. Lyakhov, and A. L. Mikhal’chuk, Khim. Geterotsikl. Soedin., 77 (2006). [Chem. Heterocycl. Comp., 42, 70 (2006)].
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Dedicated to Academician A. A. Akhrem of the Belarus Academy of Sciences on the Occasion of His Ninety-Fifth Birthday
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 335–346, March, 2008.
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Gulyakevich, O.V., Mikhal’chuk, A.L. Mechanism for annelation ([2+4] cyclocondensation) of Schiff bases by β-dicarbonyl and β,β′-tricarbonyl compounds in amphiprotic media (review). Chem Heterocycl Comp 44, 253–262 (2008). https://doi.org/10.1007/s10593-008-0041-5
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DOI: https://doi.org/10.1007/s10593-008-0041-5