Abstract
A series of quaternary ammonium salts of 5,7-dimethyl-1,3-diazaadamantan-6-one bearing aryl and alkyl substituents was synthesized. On treatment with aqueous KOH, these compounds undergo ring cleavage to give 3,7-diazabicyclo[3.3.1]nonane derivatives. The product structure was confirmed by 1H and 13C NMR and IR spectroscopy.
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References
J.-M. Lehn, Supramolecular Chemmistry. Concepts and Perspectives, VCH, Weinheim—New York—Basel—Cambridge—Tokyo, 1995.
H.-J. Schneider and A.K. Yatsimirsky, Principles and Methods in Supramolecular Chemistry, John Wiley and Sons Ltd, Chichester, England, 2000, 349 pp.
C. Janiak, J. Chem. Soc., Dalton Trans., 2003, 2871.
S. Kitagawa, R. Kitaura, and S. Noro, Angew. Chem. Int. Ed. Engl., 2004, 43, 2334.
J. B. Beck and S. J. Rowan, Polymer Preprints, 2004, 45, 79.
J. B. Beck and S. J. Rowan, J. Am. Chem. Soc., 2003, 125, 13922.
S. Weidmann, Annual Review of Physiology, 1993, 55, 1.
A. Samhammer, U. Holzgrabe, and R. Haller, Arch. Pharm. (Weinheim, Ger.), 1989, 322, 551.
G. L. Garrison, K. D. Berlin, B. J. Scherlag, R. Lazzara, E. Patterson, T. Fazekas, S. Sangiah, C. L. Chen, F. D. Schubot, and D. van der Helm, J. Med. Chem., 1996, 39, 2559; (b) M. Paroczai and E. Karpati, Pharmacol. Res., 1991, 24, 149.
P. Comba, B. Martin, A. Prikhod’ko, H. Pritzkow, and H. Rohwer, Comptes Rendus Chimie, 2005, 6, 1506; (b) P. Comba, M. Kerscher, Cryst. Eng. Comm., 2004, 6, 197; (c) S. Z. Vatsadze, V. S. Tyurin, N. V. Zyk, A. V. Churakov, L. G. Kuz’mina, E. V. Avtomonov, R. D. Rakhimov, and K. P. Butin, Izv. Akad. Nauk. Ser. Khim., 2005, 1773 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1825].
S. Z. Vatsadze, V. S. Tyurin, A. I. Zatsman, M. A. Manaenkova, V. S. Semashko, D. P. Krut’ko, N. V. Zyk, A. V. Churakov, and L. G. Kuz’mina, Zh. Org. Khim., 2006, 42, 1225 [Russ. J. Org. Chem., 2006, 55 (Engl. Transl.)].
I. Watt, S. N. Whittleton, and S. M. Whitworth, Tetrahedron, 1986, 42, 1047.
a)_L. F. Tietze, T. Eicher, Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Georg Thieme Verlag, Stuttgard—New York, 1991; b) Organikum, Organisch-chemisches Grundpraktikum, VEB Deutscher Verlag Der Wissenschaften, Berlin, 1990.
G. G. Minasyan, M. B. Mkrtchyan, and Ts. E. Agadzhanyan, Armyanskii khim. Zh. [Armenian Chem. J.], 1986, 39, 44.
G. G. Minyasyan, A. D. Arutyunyan, G. G. Adamyan, and Ts. E. Agadzhanyan, Khim. Geterotsikl. Soedinen. [Chem. Heterocycl. Comp.], 1994, 3, 401.
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Dedicated to Academician V. A. Tartakovsky on occasion of his 75th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1496–1501, August, 2007.
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Vatsadze, S.Z., Semashko, V.S., Manaenkova, M.A. et al. Study of ring cleavage in quaternary ammonium salts of 1,3-diazaadamantane. Russ Chem Bull 56, 1555–1560 (2007). https://doi.org/10.1007/s11172-007-0242-6
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DOI: https://doi.org/10.1007/s11172-007-0242-6