Abstract
A new method was developed for the synthesis of 6-substituted 1,5-diazabicyclo[3.1.0]hexanes and 7-substituted 1,6-diazabicyclo[4.1.0]heptanes by condensation of N-monohalotrimethylene- and N-monohalotetramethylenediamines with carbonyl compounds in the presence of bases. X-ray diffraction studies and quantum-chemical B3LYP/6-31G* calculations demonstrated that the conformations of the resulting bicyclic systems are stabilized by stereoelectronic interactions. As a result, a boat conformation prevails in 1,5-diazabicyclo[3.1.0]hexanes, whereas the energies of chair, half-chair, and boat conformations of 1,6-diazabicyclo[4.1.0]heptanes are equalized.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. I. Khmel´nitskii, N. N. Makhova, and O. V. Lebedev, Tez. dokl. II S'ezda farmatsevtov Latv. SSR [Abstrs. of Papers, I Conf. of Latvian Pharmaceutists], Riga, 1984, p. 81 (in Russian).
R. G. Kostyanovskii, G. V. Shustov, and O. L. Nabiev, Khim.-farm. Zh., 1986, 20, 671 [Pharm. Chem. J., 1986, 20 (Engl. Transl.)].
Ch. J. Paget and Ch. S. Davis, J. Med. Chem., 1964, 7, 626.
R. Ohme, E. Schmitz, and P. Dolge, Chem. Ber., 1966, 99, 2104.
(a) G. V. Shustov, S. N. Denisenko, I. I. Chervin, N. L. Asfandiarov, and R. G. Kostyanovsky, Tetrahedron, 1985, 41, 5719; (b) O. G. Khvostenko, B. G. Zykov, N. L. Asfandiarov, V. I. Khvostenko, S. N. Denisenko, G. V. Shustov, and R. G. Kostyanovskii, Khim. Fiz., 1985, 4, 1366 [Chem. Phys. USSR, 1985, 4 (Engl. Transl.)]; (c) G. Kaupp, S. N. Denisenko, G. V. Shustov, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 2496 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 2456 (Engl. Transl.)]; (d) R. G. Kostyanovsky, G. V. Shustov, V. V. Starovoitov, and I. I. Chervin, Mendeleev Commun., 1998, 113.
Ger. Pat. 3607993, 1987; Chem. Abstrs., 1987, 107, 236687h.
N. N. Makhova, A. N. Mikhailyuk, V. V. Kuznetsov, S. A. Kutepov, and P. A. Belyakov, Mendeleev Commun., 2000, 182.
Yu. B. Koptelov, M. Kh. Kim, A. P. Molchanov, and R. R. Kostikov, Zh. Org. Khim., 1999, 35, 116 [Russ. J. Org. Chem., 1999, 35 (Engl. Transl.)].
A. P. Molchanov, D. I. Sipkin, Yu. B. Koptelov, and R. R. Kostikov, Zh. Org. Khim., 2001, 37, 888 [Russ. J. Org. Chem., 2001, 37 (Engl. Transl.)].
V. V. Kuznetsov, N. N. Makhova, and M. O. Dekaprilevich, Izv. Akad. Nauk, Ser. Khim., 1999, 623 [Russ. Chem. Bull., 1999, 48, 617 (Engl. Transl.)].
M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Radhavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, GAUSSIAN_94, Gaussian, Inc., Pittsburgh (PA), 1995.
A. E. Reed, L. A. Curtiss, and F. Weinhold, Chem. Rev., 1988, 88, 899.
(a) U. Salzner and P. v. R. Schleyer, J. Am. Chem. Soc., 1993, 115, 10231; (b) L. Carballeira and I. Perez_Juste, J. Phys. Chem., A, 2000, 104, 9362.
G. B. Ansell, A. T. Nielsen, D. W. Moore, R. T. Atkins, and Ch. D. Stanifer, Acta Crystallogr., 1979, 35B, 1505.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kuznetsov, V.V., Kutepov, S.A., Makhova, N.N. et al. 1,5-Diazabicyclo[3.1.0]hexanes and 1,6-diazabicyclo[4.1.0]heptanes: a new method for the synthesis, quantum-chemical calculations, and X-ray diffraction study. Russian Chemical Bulletin 52, 665–673 (2003). https://doi.org/10.1023/A:1023962907733
Issue Date:
DOI: https://doi.org/10.1023/A:1023962907733