Abstract
Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 2-alkyl-3-phenylcyclopropenones gives fused polycyclic systems of the 4a,7b-diazacyclopenta[cd]inden-7-one series as a result of addition of two cyclopropenone molecules and extrusion of CO molecule. The first step of the process is characterized by 100% regioselectivity, leading to the adduct with vicinal arrangement of the aryl groups, while the regioselectivity of the second step is likely to be determined by spatial interactions between substituents in the cyclopropenone molecule and trimethylene bridge of the diazabicyclohexane. Steric hindrances in the second step could eliminate formation of stable products.
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REFERENCES
Gomaa, M.A.-M., J. Chem. Soc., Perkin Trans. 1, 2002, p. 341.
Yoshida, Z. and Konishi, H., Methoden der organischen Chemie (Houben-Weyl), Muller, E., Bayer, O., Meerwein, H., and Ziegler, K., Eds., Stuttgart: Georg Thieme, 1997, vol. E17d, p. 3019.
Deem, M.L., Synthesis, 1972, p. 675.
Matsumo, K., Kono, Y., and Uchida, T., J. Chem. Soc., Chem. Commun., 1976, p. 1045.
Matsukubo, H. and Kato, H., Chem. Lett., 1975, p. 767.
Molchanov, A.P., Sipkin, D.I., Koptelov, Yu.B., and Kostikov, R.R., Eur. J. Org. Chem., 2002, p. 453.
Koptelov, Yu.B., Kim, M.Kh., Molchanov, A.P., and Kostikov, R.R., Russ. J. Org. Chem., 1999, vol. 35, p. 110.
Molchanov, A.P., Sipkin, D.I., Koptelov, Yu.B., and Kostikov, R.R., Synlett, 2000, p. 1779.
Molchanov, A.P., Sipkin, D.I., Koptelov, Yu.B., and Kostikov, R.R., Russ. J. Org. Chem., 2001, vol. 37, p. 841.
Kascheres, A., Marchi, D., and Rodrigues, J.A.R., J. Org. Chem., 1978, vol. 43, p. 2892.
Cunha, S. and Kascheres, A., J. Mol. Struct. (Theochem), 1996, vol. 364, p. 45.
Tietze, L.-F. and Eicher, T., Reactions and Syntheses in the Organic Chemistry Laboratory, Mill Valley, California: University Science Books, 1989. Translated under the title Preparativnaya organicheskaya khimiya, Moscow: Mir, 1999, p. 275.
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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 578–585.
Original Russian Text Copyright © 2005 by Molchanov, Sipkin, Koptelov, Kostikov.
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Molchanov, A.P., Sipkin, D.I., Koptelov, Y.B. et al. Thermally Induced Tandem Cycloaddition of 2-Alkyl-3-phenylcyclopropenones to 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes. Russ J Org Chem 41, 567–574 (2005). https://doi.org/10.1007/s11178-005-0205-z
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DOI: https://doi.org/10.1007/s11178-005-0205-z