Abstract
The reactions of 1-(p-methoxyphenyl)-2-methylpropan-1-ol or α-cyclohexyl-p-methoxybenzyl alcohol with nitriles RCN in concentrated sulfuric acid afforded 1-R-3,3-dialkyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones. The stability of the latter toward the dienone-phenolic rearrangement depends on the nature of the substituent R. The reaction mechanism was studied by the semiempirical quantum-chemical AM1 method.
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V. A. Glushkov, O. G. Ausheva, G. A. Postanogova, and Yu. V. Shklyaev, Khim. Geterotsikl. Soedin., 2000, 1559 [Chem. Heterocycl. Compd., 2000 (Engl. Transl.)].
P. Balczewski, J. A. Joule, C. Estévez, and M. Alvarez, J. Org. Chem., 1994, 59, 4571.
E. V. Sadanandan, S. K. Pillai, M. V. Lakshmikantham, A. D. Billimoria, J. S. Culpepper, and M. P. Cava, J. Org. Chem., 1995, 60, 1800.
Y. Kita, T. Takada, M. Gyoten, H. Tohma, M. H. Zenk, and J. Eichhorn, J. Org. Chem., 1996, 61, 5857.
N. A. Braun, M. A. Ciufolini, K. Peters, and E.-M. Peters, Tetrahedron Lett., 1998, 39, 4667.
S. Hirotani and E. Kaji, Tetrahedron, 1999, 55, 4255.
G. V. Gavrilova, D. P. Krut'ko, A. A. Gavrilov, and K. P. Butin, Izv. Akad. Nauk, Ser. Khim., 1997, 1015 [Russ. Chem. Bull., 1997, 46, 975 (Engl. Transl.)].
A. M. Fivush and S. R. Strunk, Synth. Commun., 1996, 26, 1623.
Y. Nagao, W. S. Lee, I. Y. Jeong, and M. Shiro, Tetrahedron Lett., 1995, 36, 2799.
V. A. Glushkov, Yu. V. Shklyaev, V. I. Sokol, V. S. Sergienko, and V. V. Davidov, Mendeleev Commun., 1998, 227; 1999, 170.
V. S. Shklyaev, B. B. Aleksandrov, G. I. Legotkina, M. I. Vakhrin, M. S. Gavrilov, and A. G. Mikhailovskii, Khim. Geterotsikl. Soedin., 1983, 1560 [Chem. Heterocycl. Compd., 1983, 1242 (Engl. Transl.)].
H. Wollweber and R. Hiltman, Angew. Chem., 1960, 72, 1001.
L. I. Krimen and D. J. Cota, Org. React., 1969, 17, 213.
J. J. Ritter and J. K. Minari, J. Am. Chem. Soc., 1948, 70, 4045.
J. P. Gavin and R. D. Waigh, J. Chem. Soc., Perkin Trans. 1, 1990, 503.
S. Doi, N. Shirai, and Y. Sato, J. Chem. Soc., Perkin Trans. 1, 1997, 2217.
M. J. S. Dewar, E. G. Zoeblisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
M. S. Gavrilov, B. B. Aleksandrov, V. S. Shklyaev, and Yu. V. Shklyaev, Materialy Vtoroi Regional'noi konferentsii “Enaminy v organicheskom sinteze” [Abstracts of Papers, II Regional Conference on Enamines in Organic Synthesis], Perm, Russia, 1991, 31 (in Russian).
F. A. Carroll and G. S. Hammond, Isr. J. Chem., 1972, 10, 613.
J. J. P. Stewart, MOPAC, Version 7.0, Frank J. Seiler Research Laboratory, US Air Force Academy, QCPE 175.
J. Schmidlin and R. V. Escher, Ber., 1912, 45, 889.
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Ausheva, O.G., Glushkov, V.A., Shurov, S.N. et al. Spirocyclohexadienones. 4. Synthesis and dienone-phenolic rearrangement of 1-R-3,3-dialkyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones. Russian Chemical Bulletin 50, 1648–1656 (2001). https://doi.org/10.1023/A:1013051005590
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DOI: https://doi.org/10.1023/A:1013051005590