Abstract
The reaction of N-phenylbenzamidine with O-acetylbenzeneoximoyl chloride in methanol solution gave unexpectedly 5-methoxy-3,4,5-triphenyl-4,5-dihydro-1,2,4-oxadiazole, which structure was confirmed by X-ray analysis. The last step of this reaction was simulated by the PM3 semiempirical method.
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REFERENCES
D. W. Fry, A. J. Kraker, A. McMichael, L. A. Ambroso, J. M. Nelson, W. R. Leopold, R. W. Connors, and A. J. Bridges, Science, 265, 1093 (1994).
S. W. Wright, D. L. Hageman, L. D. McClure, A. A. Carlo, J. L. Treadway, A. M. Mathiowetz, J. M. Withka, and P. H. Bauer, Bioorg. Med. Chem. Lett., 11, 17 (2001).
W. Szczepankiewicz and J. Suwinski, Tetrahedron Lett., 39, 1785 (1998).
W. Szczepankiewicz and J. Suwinski, R. Bujok, Tetrahedron, 56, 9343 (2000).
J. Suwinski and M. A. A. Mohamed, Polish J. Chem., 75, 965 (2001).
W. Szczepankiewicz, J. Suwinski, T. Borowiak, M. Kubicki, and P. Wagner, Polish J. Chem., 76, 1137 (2002).
C. De Micheli, R. Gandolfi, and P. Grunanger, Tetrahedron, 30, 3765 (1974).
W. Szczepankiewicz, J. Suwinski, and J. Slowikowska, Acta Crystallogr., C55, 2158 (1999).
E. Carvalfo, J. Iley, and E. Rosa, J. Chem. Soc., Chem. Commun., 1249 (1988).
J. P. P. Stewart, Mopac 2000.00 Manual, Fujitsu Limited, Tokyo, 1999.
M. J. S. Dewar and W. Thiel, J. Am. Chem. Soc., 99, 4899 (1977).
D. M. Dolney, G. D. Hawkins, P. Wignet, D. A. Liotard, C. J. Cramer, and D. G. Truhlar, J. Comput. Chem., 21, 340 (2000).
A. Klamt and G. Schürmann, J. Chem. Soc., Perkin Trans. 2, 799 (1993).
F. Rived, M. Roses, and E. Bosch, Anal. Chim. Acta, 374, 309 (1998).
M. J. S. Dewar, E. G. Zoebish, E. F. Helay, and J. P. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).
Y. H. Chiang, J. Org. Chem., 36, 2146 (1971).
KUMA Diffraction. KM4 User's Guide. Version 3.2. KUMA Diffraction, Wrocław, Poland, 1991.
Z. Galdecki, A. Kowalski, and L. Uszynski, DATAPROC the Data Processing Program. Version 9.0. KUMA Diffraction, Wroclaw, Poland, 1995.
G. M. Sheldrick, Acta Crystallogr., A46, 467 (1990).
G. M. Sheldrick, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, Göttingen, 1993.
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Szczepankiewicz, W., Suwinski, J. & Karczmarzyk, Z. Reaction of N-Phenylbenzamidine with O-Acetylbenzeneoximoyl Chloride. Chemistry of Heterocyclic Compounds 40, 801–806 (2004). https://doi.org/10.1023/B:COHC.0000040779.25858.e3
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DOI: https://doi.org/10.1023/B:COHC.0000040779.25858.e3