Synthesis, Characterization, Stereochemistry and Antimicrobial Evaluation of N-Acyltetrahydrobenzodiazepin-2-ones | Zendy

A. Akila | Zendy; P. Sakthivel | Zendy; S. Ponnuswamy | Zendy

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Synthesis, Characterization, Stereochemistry and Antimicrobial Evaluation of N-Acyltetrahydrobenzodiazepin-2-ones

Author(s) -

A. Akila,

P. Sakthivel,

S. Ponnuswamy

Publication year - 2020

Publication title -

asian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.145

H-Index - 34

eISSN - 0975-427X

pISSN - 0970-7077

DOI - 10.14233/ajchem.2020.22331

Subject(s) - chemistry , conformational isomerism , heteronuclear single quantum coherence spectroscopy , antimicrobial , ring flip , stereochemistry , dept , coupling constant , ring (chemistry) , proton nmr , carbon 13 nmr , specific rotation , chemical shift , spectral analysis , spectral properties , computational chemistry , two dimensional nuclear magnetic resonance spectroscopy , molecule , organic chemistry , physics , particle physics , quantum mechanics , spectroscopy

A few N5-substituted (1) and N1,N5-disubstituted tetrahydro-1,5-benzodiazepin-2-ones (2-8) viz. N5-chloroacetyl-, N5-formyl-, N5-dichloro-acetyl-, N1,N5-diethoxycarbonyl-, N1,N5-bischloroacetyl-, N5-piperazinoacetyl- and N5-morpholinoacetyltetrahydro-1,5-benzodiazepin-2-ones have been synthesized. The characterization and conformational analysis of these compounds 2-8 have been carried out using IR and 1H, 13C, DEPT & 2D (COSY & HSQC) NMR spectral techniques. The coupling constants for compounds 3-6 were determined by irradiating the C4-methyl doublet. The appearance of major and minor conformers has been found in the case of benzodiazepin-2-ones (3 and 6) and the spectral data confirm the equilibrium due to ring inversion over the N-C=O rotation. The spectral data and the extracted coupling constant values revealed that the substituted tetrahydro-1,5-benzodiazepin-2-ones (2-8) prefer to adopt boat conformation. The antimicrobial activity of compounds 1-8 has also been evaluated.

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