A Convenient Method for the Synthesis of 1,5-benzodiazepin-2-one

Rida, Maurice Abou; Meslouhi, H. El; Ahabchane, Noureddine Hamou; Garrigues, Bernard; Es-Safi, Nour Eddine; Essassi, E. M.

doi:10.2174/1874095200801020083

Cited by 6 publications

(4 citation statements)

References 24 publications

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“…General Procedures 2.1.1. Synthesis of 3-Hydroxy-4-phenyl tetrahydro-1,5-benzodiazepin-2-one (3) 1,5-benzodiazepine diastereoisomers, 3a and 3b, were prepared according to the procedure described by our team through the condensation of 4,5-dimethyl-o-phenylenediamine with ethyl phenyl glycidate in refluxing xylene for 48 h (Scheme 1) [24,25].…”

Section: Methodsmentioning

confidence: 99%

“…These compounds have been synthesized according to the procedure previously described in reference [24].…”

Section: Cis 3bmentioning

confidence: 99%

“…The structure of the two diastereoisomeric compounds, 3a and 3b, were first characterized using 1 H NMR spectroscopy [24,25], and the configuration of each diastereoisomer was established through the coupling constant between the proton atoms at positions 3 and 4 of the seven-membered ring. The 1 H NMR spectrum of compound 3a showed two doublets with a coupling constant of 10 Hz corresponding to the trans configuration.…”

Section: Structural Elucidation Of Compounds 3a 3b 4 Andmentioning

confidence: 99%

“…To confirm the results of the 1HNMR spectroscopy, we performed a single-crystal X-ray diffraction study of compound 3b. Furthermore, 1-ethyl-3-hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one 4 and trans dialkylated -1,5-benzodiazepin-2-one 5 were synthesized according to the procedure described by Rida et al [24] (Scheme 2). Scheme 2.…”

Section: Structural Elucidation Of Compounds 3a 3b 4 Andmentioning

confidence: 99%

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X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

Lahmidi,

Bakheit,

Essassi

et al. 2023

Crystals

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This study investigated the crystallographic and electronic properties of 1,5-benzodiazepine compounds, namely: cis-(3S,4S)-3-hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 3b, trans-(3R,4R)-1-ethyl-3-hydroxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one 4, and trans-(3S,4S) 1-ethyl-3-ethoxy-7,8-dimethyl-4-phenyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one 5. Hirshfeld surface analysis was also applied to discern the intermolecular interactions, highlighting the significance of hydrogen bonding, van der Waals forces, and the influence of specific substituents. Furthermore, the MESP maps created using the density functional theory revealed the electrostatic nature of these molecules. The absence of dark blue regions on the MESP maps and variations due to different functional groups and substitutions were noteworthy findings. Collectively, this research offers crucial insights into the behaviour, interactions, and potential applications of new compounds. Finally, the anticancer effects of compounds 3b, 4, and 5 were evaluated against three cancer cell lines and one normal cell line, and the results showed that 3b and 4 had potent antiproliferative effects against all three cancer cell lines.

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Section: Methodsmentioning

confidence: 99%

“…These compounds have been synthesized according to the procedure previously described in reference [24].…”

Section: Cis 3bmentioning

confidence: 99%

Section: Structural Elucidation Of Compounds 3a 3b 4 Andmentioning

confidence: 99%

Section: Structural Elucidation Of Compounds 3a 3b 4 Andmentioning

confidence: 99%

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X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

Lahmidi,

Bakheit,

Essassi

et al. 2023

Crystals

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First Highly Enantioselective Synthesis of Benzodiazepinones by Catalytic Hydrogenation

2010

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Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction

Fang

Cao

Sun

et al. 2018

Chemistry A European J

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An NHC-catalyzed formal [3+4] annulation of α,β-unsaturated acylazoliums with protecting-group-free aryl 1,2-diamines was developed for a direct and highly enantioselective synthesis of 4-aryl N-H-free 1,5-benzodiazepin-2-ones. This methodology offers an efficient and rapid access to a wide range of enantioenriched target compounds from easily accessible starting materials. The protocol is also scalable and the desired products can easily undergo subsequent N-functionalization to afford diverse N-substituted derivatives. Additionally, a mechanism was proposed to explain the high enantioselectivity in this process.

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A Convenient Method for the Synthesis of 1,5-benzodiazepin-2-one

Cited by 6 publications

References 24 publications

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

X-ray Crystal Structure, Hirshfeld Surface Analysis, DFT, and Anticancer Effect of 3-Hydroxy-4-phenyl-1,5-benzodiazepin-2-one Derivatives

First Highly Enantioselective Synthesis of Benzodiazepinones by Catalytic Hydrogenation

Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction

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