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Synthesis and X-ray diffraction data of 6,8-dimethyl-cis-2-vinyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol and 8-chloro-9-methyl-cis-2-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol

Published online by Cambridge University Press:  05 March 2012

M. A. Macías ,
J. A. Henao ,
Lina María Acosta  and
Alirio Palma
M. A. Macías
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
J. A. Henao*
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
Lina María Acosta
Affiliation:
Laboratorio de Síntesis Orgánica (LSO), Centro de Investigación en Biomoléculas, (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
Alirio Palma
Affiliation:
Laboratorio de Síntesis Orgánica (LSO), Centro de Investigación en Biomoléculas, (CIBIMOL), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
*
a)Author to whom correspondence should be addressed. Electronic mail: jahenao@uis.edu.co
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Abstract

The 6,8-dimethyl-cis-2-vinyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol (2a) (Chemical formula C14H19NO) and 8-chloro-9-methyl-cis-2-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ol (2b) (Chemical formula C14H18ClNO) were prepared via the reductive cleavage of the bridged N-O bond of the corresponding 1,4-epoxytetrahydro-1-benzazepines. The X-ray powder diffraction patterns for the new compounds were obtained. The compound 2a was found to crystallize in an orthorhombic system with space group Pmn21 (No. 31), refined unit-cell parameters a = 19.422(6) Å, b = 6.512(3) Å, c = 9.757(4) Å and V = 1234.0(5) Å3. The compound 2b was found to crystallize in a monoclinic system with space group P21/m (No. 11), refined unit-cell parameters a = 17.570(4) Å, b = 8.952(3) Å, c = 14.985(4) Å, β = 101.66(2)°, and V = 2308.3(9) Å3.

Keywords

tetrahydro-1-benzazepineX-ray powder diffraction dataantiparasitic agents
Type
New Diffraction Data
Information
Powder Diffraction , Volume 26 , Issue 4 , December 2011 , pp. 346 - 349
Copyright
Copyright © Cambridge University Press 2011

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References

Acosta, L. M., Palma, A., and Bahsas, A. (2010). “Rational use of substituted N-allyl and N,N-diallylanilines in the stereoselective synthesis of novel 2-alkenyltetrahydro-1-benzazepines,” Tetrahedron 66, 8392–8401.10.1016/j.tet.2010.08.067CrossRefGoogle Scholar
Buhrke, V., Jenkins, R., and Smith, D. (1998). Preparation of Specimens for X-ray Fluorescence and X-ray Diffraction Analysis (Wiley, New York), pp. 141–142.Google Scholar
Boultif, A., and Loüer, D. (2006). “Indexing of powder diffraction patterns of low symmetry lattices by successive dichotomy method,” J. Appl. Crystallogr. 37, 724–731.10.1107/S0021889804014876CrossRefGoogle Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr. 1, 108–113.10.1107/S002188986800508XCrossRefGoogle Scholar
Dong, C. (1999). “PowderX: Windows-95-based program for poder X-ray diffraction data processing,” J. Appl. Crystallogr. 32, 838–838.10.1107/S0021889899003039CrossRefGoogle Scholar
Gómez-Ayala, S., Castrillón, J. A., Palma, A., Leal, S. M., Escobar, P., and Bahsas, A. (2010). “Synthesis, structural elucidation and in vitro antiparasitic activity against Trypanosoma cruzi and Leishmania chagasi parasites of novel tetrahydro-1-benzazepine derivatives,” Bioorg. Med. Chem. 18, 4721–4739.10.1016/j.bmc.2010.05.018CrossRefGoogle Scholar
Gómez-Ayala, S. L., Stashenko, E., Palma, A., Bahsas, A., and Amaro-Luis, J. M. (2006). “Sequential amino-claisen rearrangement/intramolecular 1,3-Dipolar cycloaddition/reductive cleavage approach to the stereoselective synthesis of cis-4-hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1H)-benzazepines,” Synlett 14, 2275–2277.Google Scholar
Knockaert, M., Wieking, K., Schmitt, S., Leost, M., Grant, K. M., Mottram, J. C., Kunick, C., and Meijer, L. (2002). “Intracellular Targets of Paullones,” J. Biol. Chem. 277, 25493–25501.10.1074/jbc.M202651200CrossRefGoogle ScholarPubMed
Laugier, J. and Bochu, B. (2002). CHEKCELL. “LMGP-suite suite of programs for the interpretation of X-ray. Experiments,” ENSP/Laboratoire des Matériaux et du Génie Physique, BP 46. 38042 Saint Martin d’Hères, France. http://www.inpg.fr/LMGP and http://www.ccp14.ac.uk/tutorial/lmgp/.Google Scholar
Matthews, J. M., Greco, M. N., Hecker, L. R., Hoekstra, W. J., Andrade-Gordon, P., de Garavilla, L., Demarest, K. T., Ericson, E., Gunnet, J. W., Hageman, W., Look, R., Moore, J. B., and Maryanoff, B. E. (2003). “Synthesis and biological evaluation of novel indoloazepine derivatives as non-peptide vasopressin V2 receptor antagonists,” Bioorg. Med. Chem. Lett. 13, 753–756.10.1016/S0960-894X(02)01059-4CrossRefGoogle ScholarPubMed
Miguell, A. D., Hubberd, C R., and Stalick, J. K. (1981). “NBS* AIDS80: A FORTRAN program for crystallographic data evaluation,” National Bureau of Standards (USA), Tech. Note 1141.Google Scholar
Palma, A., Yépes, A. F., Leal, S. M., Coronado, C. A., and Escobar, P. (2009). “Synthesis and in vitro activity of new tetrahydronaphtho[1,2-b]azepine derivatives against Trypanosoma cruzi and Leishmania chagasi parasites,” Bioorg. Med. Chem. Lett. 19, 2360–2363.10.1016/j.bmcl.2008.05.013CrossRefGoogle Scholar
Rachinger, W. A. (1948). “A Correction for the α1 α2 Doublet in the Measurement of Widths of X-ray Diffraction Lines,” J. Sci. Instrum. 25, 254.10.1088/0950-7671/25/7/125CrossRefGoogle Scholar
Saviztky, A. and Golay, M. J. (1964). “Smoothing and differentiation of data by simplified least squares procedures,” Anal. Chem. 36, 1627–1639.10.1021/ac60214a047Google Scholar
Schultz, C., Link, A., Leost, M., Zaharevitz, D. W., Gussio, R., Sausville, E. A., Meijer, L., and Kunick, C. (1999). “Paullones, a Series of Cyclin-Dependent Kinase Inhibitors: Synthesis, Evaluation of CDK1/Cyclin B Inhibition, and in vitro Antitumor Activity,” J. Med. Chem. 42, 2909–2919.10.1021/jm9900570CrossRefGoogle ScholarPubMed
Shimada, Y., Taniguchi, N., Matsuhisa, A., Sakamoto, K., Yatsu, T., and Tanaka, A. (2000). “Highly potent and orally active non-peptide arginine vasopressin antagonists for both V1A and V2 receptors: Synthesis and pharmacological properties of 4′-[(4,4-Difluoro-5-methylidene-2,3,4,5-tetrahydro-1H-1-benzoazepin-1-yl)carbonyl]-2-phenyl-benzanilide derivatives,” Chem. Pharm. Bull. 48, 1644.CrossRefGoogle Scholar
Smith, G. S. and Snyder, R. L. (1979). “F N: A criterion for rating powder diffraction patterns and evaluating the reliability of powder-pattern indexing,” J. Appl. Crystallogr. 12, 60–65.10.1107/S002188987901178XCrossRefGoogle Scholar
Sonneveld, E. J. and Visser, J. W. (1975). “Automatic collection of powder diffraction data from photographs,” J. Appl. Crystallogr. 8, 1–7.10.1107/S0021889875009417CrossRefGoogle Scholar
Zuccotto, F., Zvelebil, M., Brun, R., Chowdhury, S. F., Di Lucrezia, R., Leal, I., Maes, L., Ruiz-Perez, L. M., Pacanowska, D. G., and Gilbert, I. H. (2001). “Novel inhibitors of Trypanosoma cruzi dihydrofolate reductase,” Eur. J. Med. Chem. 36, 395–405.10.1016/S0223-5234(01)01235-1CrossRefGoogle ScholarPubMed