4-Phenyl-1,5-benzodiazepin-2-one Compound as a Precursor of Various New heterocyclic Systems with Potent pharmacological Properties
DOI:
https://doi.org/10.34874/IMIST.PRSM/fsejournal-v1i1.26874Keywords:
4-‐phenyl-‐1, 5-‐benzodiazepin-‐2-‐one, hydrogenation, hydrogenolysis, alkylation, cycloaddidtion, isoxazole, isoxazolineAbstract
Various new heterocyclic compounds were synthesized starting from 4-phenyl-1,5-benzodiazepin-2-one. Catalytic hydrogenation was first explored leading to the formation of compounds where the diazepinic seven bond ring was or was not
opened.
Further
alkylation
reactions
of
the
new
formed
derivatives
were
achieved
in
order
to
prepare new dipolarophile adducts with two substituted diazepinic nitrogen atoms. Final cycloaddition reactions were conducted giving new heterocyclic compounds containing five membered ring in the 5 position of the benzodiazepine skeleton. New molecules containing isoxazolic and isoxazolinic skeletons were thus obtained through the action of arylnitriloxides on the double and triple bonds. The double C=O bond was shown to be inactive on the used dipoles and in the used conditions. The structures of all the new synthesized compounds were elucidated on the basis of Mass spectrometry, NMR (1H, 13C) spectroscopy and X-ray diffraction analysis. The prepared isoxazolic compounds are expected to possess various pharmacological properties.
References
E.M.Essassi, M. Salem. Synthèse des pyrazolyl-1 benzimidazoles à partir des benzodiazépin-‐1,5-ones-2. Bull. Soc. Chim. Belg., (1985), 94, 755.
E.M. Essassi, M. Salem, Ph. Viallefont. Action de l'hydroxylamine sur les dihydro- 1,3-benzodiazépine-1,5- thiones (ones) -2. Bull. Soc. Chim. France, (1987), 890.
E.M. Essassi, M. El Abbassi, J. Fifani. Synthèse des benzimidazolyl-2 méthyl-5 pyrazolyl-3 méthane à partir des acetylmethylène-4 benzodiazépin-1,5 ones-2. Bull. Soc. Chim. Belg., (1987), 96, 225.
E.M. Essassi, M. Salem. Synthèse des pyrazolo[2,3-b] triazépines-1,3,5 à partir des alkyl-1 benzodiazépin-1,5 ones-‐2. Bull. Soc. Chim. Belg., (1988), 97, 387.
M. El Abbassi, E.M. Essassi, J. Fifani, E.M. Tjiou. Synthèse des pyrazolo [2',3' : 1,7] diazépino-1,4 -‐benzimidazoles et des 1- lkyl-‐ -[(5-‐méthyl-3-pyrazolyl)] méthyl benzimidazoles. Bull. Soc. Chim. Fr., (1990), 127, 117.
E.M. Essassi. L'utilisation des 1,5- enzodiazépines en synthèse hétérocyclique. Bull. Soc. Chim. Belg., (1994), 103, 679.
B. El Azzaoui, J. Fifani, E.M. Tjiou, E.M. Essassi, J. Jaud, L. Lopez, J.Bellan. Synthèse et mise en évidence par spectrométrie de masse (FAB) des propriétés complexantes du 2-‐(5-‐méthyl-1-yridin-2-yl-‐pyrazol-3-yl)méthyl benzimidazole et d'une réaction d'oxydation par l'oxygène moléculaire. Tetrahedron lett., (1999), 40, 4667.
N. H. Ahabchane, A. Keita, E.M. Essassi. Synthèse des 1-pyrazolyl, isoxazolyl et 1,2,3-triazolylméthyl-‐1,5-‐benzodiazépine par cycloaddition dipolaire -‐1,3. C.R.Acad. Paris, Série IIc, (1999), 591.
N. Hamou Ahabchane, E.M. Essassi, L. Lopez, J. Bellan, L. Lamande. Synthèse de
nouveaux macrocycles dérivés de la 1-‐pyrazolyl-‐benzimidazole-‐2-‐thione. Phosphorus, Sulfur and Silicon, (2001), 173,175.
N. Hamou Ahabchane, S. Ibrahimi, M. Salem, E. M. Essassi, S. Hamzazi , A. BENJOUAD. Synthèse et
propriétés biologiques des pyrazolo [4,3-‐b] triazolo[4,3-a][1,5]benzodiazépines. C. R. Acad. Sci. Paris, Série IIc, (2001), 4, 917.
J. T. Ghomsi, N. Hamou Ahabchane, E. M. Essassi. Synthesis of novel 1,5-‐ benzodiazepines associated with different five-‐memberd-‐heterocycles. Phosphorus, Sulfur and Silicon, (2004), 179, 353.
J. T. Ghomsi, N. Hamou Ahabchane, N. Es-‐Safi, B. Garrigues, E. M. Essassi. Synthesis and Spectroscopic Structural elucidation of new quinoxaline derivatives Spectroscopy Letters, (2007), 40, 741.
M. L. Doumbia, R. Bouhfid, N. Hamou Ahabchane, E. M. Essassi. A convenient synthesis of new pyrazolylquinoxalines from 1,5-‐benzodiazepine-‐2-‐thione. ARKIVOC, (2008), XIII, 36-‐44.
M. L. Doumbia, R. Bouhfid, E. M. Essassi, L. El Ammari. N-‐(5-‐Phenyl-‐1H-‐pyrazol-3-yl)benzene-1,2-diamine. Acta Cryst. (2010), E66, o 841
A. Rossi, A. Hunger, G. Kebrle, K. Hoffman. Helvetica Chemica Acta, (1960), 163, 1298.
R. Achour, E. M. Essassi, R. Zniber. Bull. Soc. Chim. Fr. (1988), 5, 889.
H. R. Morales, A. Bulbarela et R. Contreras, J. Heterocyclic Chem., (1986), 24, 135.
G. A. Lee. Synthesis, (1982), 508.
S. H. Hwang, M. J. Kurth. Tetrahedron letters, (2002), 43, 53-‐56.
G. Terrago, A. Ramdani, J. Elguero, M. Espader. J. Heterocyclic Chem., (1980), 17, 137.
R. K. Howe, F. M. Schleppnik. J. Heterocyclic Chem., (1982), 19, 721.
S. Kirkiacharian. Guide de Chimie Thérapeutique, édition Ellipses, 243, (1996).
