SYNTHESIS OF NEW BENZIMIDAZOLE DERIVATIVES FROM 1,5- BENZODIAZEPINES THROUGH A NEW REARRANGEMENTS IN THE PRESENCE OF DMF-DMA AND HYDRAZINE HYDRATE

M. L. Doumbia, D. Ballo, N. Hamou Ahbchane, Y. El Bakri, K. Misbahi, Y. Kandri Rodi, E.M. Essassi

Abstract


We study in this work the condensation of DMF-DMA with 4-phenyl-1,5-benzodiazépin-2- one and 4-phenyl-1,5-benzodiazépine-2-thione derivatives . The results obtained showed that the 1,5-benzodiazepines used as starting materials reacted differently towards DMF-DMA. Thus 4-phenyl-1,5-benzodiazepin-2-one 1,3 leads to the target compounds namely 3-dimethylaminovinyl-4-phenyl-1,5-benzodiazepin-2-ones 2,4 while 4-phenyl-1,5- benzodiazepine-2-thione 8 affords 2-methoxy-1-phenyethylidene-benzimidazole 10. Moreover, the condensation of hydrazine hydrate with 3-dimethylaminovinyl-4-phenyl-1,5- benzodiazepin-2-one derivatives 2 and 4 gives the corresponding pyrazolic compounds 5 and 6. Furthermore 1-benzyl-3-dimethylaminovinyl-4-phenyl-1,5-benzodiazepine-2-thione 9 reacted with hydrazine hydrate to lead to 1-benzyl- 2-(pyrazol-4-3(5)-phenyl)-benzimidazole 7 which was also obtained by heating compound 6 in refluxing n-butanol. The mechanisms of the all reactions studied have been proposed and discussed.

Keywords


1,5-benzodiazepines / DMF-DMA / benzimidazole / pyrazole / rearrangement.

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DOI: https://doi.org/10.48369/IMIST.PRSM/jmch-v21i03.37465

ISSN Online : 2605-5996  

 

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