Three 1,5-benzodiazepines viz., 𝑁5-chloroacetyl-, 𝑁5-piperazinoacetyl- and N5 -morpholinoacetyl-2,2,4-trimethyl-1H-1,5-benzodiazepines have been synthesized. The structural characterisation and the conformational preferences of the compounds have been carried out using IR, 1D and 2D NMR spectral data. The NMR spectral data show that the 𝑁-acetyltetrahydro-1,5-benzodiazepines prefer to exist in boat conformation with exo orientation of >C=O at 𝑁5 position in the solution state. The X-ray crystal structure of 𝑁5-morpholinoacetyl-2,2,4-trimethyl-1H-1,5-benzodiazepine also supports boat conformation in the solid state. The antimicrobial activity for 𝑁-acetyltetrahydro-1,5-benzodiazepines have been carried out. 𝑁-morpholinoacetyl-2,2,4-trimethyl-1H-1,5-benzodiazepine demonstrated better antibacterial and antifungal activities.
Volume 134, 2022
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