The interaction of 2,5-dialkylphenols (2,5-dimethylphenol and 2-isopropyl-5-methylphenol) with isobutyric aldehyde and nitriles in the presence of concentrated sulfuric acid as catalyst resulted in the formation of 1-R-9-alkyl-3,3,6-trimethyl-2-azaspiro[4.5]deca-6,9-dien-8-ones and 1-R-9-alkyl-3,3,6-trimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. A. Glushkov, O. G. Ausheva, S. N. Shurov, and Yu. V. Shklyaev, Izv. Akad. Nauk, Ser. Khim., 822, (2002). [Russ. Chem. Bull., Int. Ed., 51, 894 (2002).]
Yu. V. Nifontov, V. A. Glushkov, O. G. Ausheva, and Yu. V. Shklyaev, Zh. Org. Khim., 38, 1437 (2002). [Russ. J. Org. Chem., 38, 1386 (2002).]
O. G. Stryapunina, I. V. Plekhanova, O. A. Maiorova, V. A. Glushkov, and Yu. V. Shklyaev, Zh. Org. Khim., 44, 1778 (2008). [Russ. J. Org. Chem., 44, 1752 (2008).]
V. A. Glushkov, O. G. Stryapunina, A. A. Gorbunov, O. A. Maiorova, P. A. Slepukhin, S. Ya. Ryabukhina, E. V. Khorosheva, V. I. Sokol, and Yu. V. Shklyaev, Tetrahedron, 66, 721 (2010).
Yu. V. Shklyaev, Yu. V. Nifontov, A. S. Shashkov, and S. I. Firgang, Izv. Akad. Nauk, Ser. Khim., 2075 (2002). [Russ. Chem. Bull., Int. Ed., 51, 2234 (2002).]
Yu. S. Rozhkova, K. A. Galata, T. S. Vshivkova, and Yu. V. Shklyaev, Zh. Org. Khim., 49, 1070 (2013). [Russ. J. Org. Chem., 49, 1055 (2013).]
Yu. S. Rozhkova, K. A. Khmelevskaya, Yu. V. Shklyaev, M. A. Ezhikova, and M. I. Kodess, Zh. Org. Khim., 48, 75 (2012). [Russ. J. Org. Chem., 48, 69 (2012).]
J. C. Martini, N. W. Franke, and G. M. Singerman, J. Org. Chem, 35, 2904 (1970).
L. A. Carpino, H. Shroff, S. A. Triolo, E. M. E. Mansour, H. Wenschuh, and F. Albericio, Tetrahedron Lett., 34, 7829 (1993).
D. Vaughan and A. Jha, Tetrahedron Lett., 50, 5709 (2009).
This work was performed with financial support from the Russian Foundation for Basic Research (grants 11-03-00367, 12-03-33-135, 13-03-00184).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 228-234, February, 2014.
Rights and permissions
About this article
Cite this article
Rozhkova, Y.S., Galata, K.A., Vshivkova, T.S. et al. A Three-Component Condensation of 2,5-Dialkyl-Phenols, Isobutyric Aldehyde, and Nitriles. Synthesis of New 2-Azaspiro[4.5]Deca-6,9-Dien-8-Ones and 2-Azaspiro[4.5]Deca-1,6,9-Trien-8-Ones. Chem Heterocycl Comp 50, 204–210 (2014). https://doi.org/10.1007/s10593-014-1462-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-014-1462-y