Halogenacylphenole durch BF<sub>3</sub>‐Kondensation

Oelschläger, H.; Moussa, O.

doi:10.1002/ardp.19733061103

Cited by 5 publications

(1 citation statement)

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“…The synthesis of the title compound was prompted by the observations of Chen (1963) and Oelschlager and Giebenhain (1973), that hydrogenated benzimidazoles may show much stronger biological activity than their unsaturated parents. The compound is both a (cyclic) thiourea and a thiocarbanilide derivative and the two classes have their representatives among known tubercuiostatics.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures ofcis andtrans 7-phenylcarbamoyl-7,9-diazabicyclo [4.3.0] nonan-8-thiones

1994

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CI4HITN3OS, M r = 275.37, CAD4F diffractometer, Cu Kc~, T = 293K. cis: orthorhombic. Fdd2, a = 22.166(2), b = 48.948(3), and c = 5.165(1),~,; final R = 0.045 for 2519 observed reflec--tions. trans: triclinic, PT, a = 11.375(2), b = 11.388(2), c = 11.823(I)A, e~ = 110.72(I), /3 = 89.97(I) and 3' = 93.86(2)~ final R = 0.043 for 3993 observed reflections. Structures were solved with direct methods and refined by full-matrix Ibast-squares with anisotropic thermal parameters for non-H-atoms. The molecules of the studied isomers have very similar conformations. except for the obvious difference in the bicyclic system junction. Similar orientations of a flexible phenylcarbamoyl substituent results from an intramolecular hydrogen bond S--. H--N(carbamoyl). Generally, molecules of the trans form are flat and those of cis are not. The observation may be of pharmacological importance as the trans isomer is a far more potent tuberculostatic agent than the cis.

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Section: Introductionmentioning

confidence: 99%