A new rearrangement of fused tetracyclic heterocycles in an acidic medium in the presence of NaBH3CN

Tetrahedron Letters

Volumn 47, Issue 46, 2006, Pages 8157-8159

  Zachová, Hana ^a   Marek, Radek ^a   Man, Stanislav ^a   Taraba, Jan ^a   Potáček, Milan ^a  

^a MASARYK UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; SODIUM DERIVATIVE;

ACIDITY; ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 33749517307     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.030     Document Type: Article

References (14)

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11. Borch R.F., Bernstein M.D., and Durst H.D. J. Am. Chem. Soc. 93 (1971) 2897-2904
12. Crystals were obtained from chloroform solution by evaporation. The diffraction data for compound 3′b were collected on a KUMA KM-4 CCD kappa-axis diffractometer using graphite monochromatized Mo-Kα radiation (λ = 0.71069 Å). The structure was solved by direct methods (Sheldrick G.M.: SHELX-97 program package, University of Goettingen 1997, Sheldrick G.M.: SHELXTL V 5.1, Bruker AXS GmbH.) Nonhydrogen atoms were refined anisotropically, while hydrogen atoms were inserted in calculated positions and isotropically refined assuming a 'ride-on' model (Fig. 1). In the symmetrical independent part of a unit cell there are two slightly different molecules of 3′b and six molecules of chloroform. The crystal structure of 3′b is without any strong H-bonding except for N-H⋯Cl (1.888 Å) and N-H⋯N (2.131 Å) contacts. The crystal packing of 3′b contains periodically alternating coplanar planes of molecules of 3′b (plane A) and chloroform solvent molecules (plane B). The structural motive is ABAB. The orientation of these planes is F(1 0 1). The crystal packing is shown in Figure 2. Crystallographic data for compound 3′b have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, under No. CCDC 601780.
13. In an alkaline medium oily products are formed, which were not easily isolable. When the crystalline products are heated dry, they readily lost HCl and formed products with a variable content of HCl.
14. 13C NMR at 75.5 MHz.