Racemic 9,10-dimethoxy-3-methyl-6-phenyl-7,7a-dihydrobenzo[<i>b</i>]benzo[4,5]isothiazolo[2,3-<i>d</i>][1,4]diazepine 12,12-dioxide

Bassin, Jatinder P.; Shah, Virender P.; Martin, Lee

doi:10.1107/s1600536811004983

Cited by 2 publications

(1 citation statement)

References 17 publications

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“…Our interest in the synthesis of heterocyclic rings fused to medium sized rings led us to envisage a straightforward synthetic approach to the benzo[6,7][1,5]diazocine[2,1- a ]isoindol-12-(14 H )-one ring system [38,39]. A number of 3-(2-oxo-2-phenylethyl) isobenzofuran-1(3 H )-ones 4a – m were synthesized following the reported literature procedures [40,41,42,43,44,45,46,47,48,49,50,51] (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

et al. 2016

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Abstract:A simple synthetic route affording 27%-85% yields of benzo [6,7][1,5]diazocino[2,1-a]isoindol-12(14H)-one ring systems from readily available 3-(2-oxo-2-phenylethyl) isobenzofuran-1(3H)-ones and 2-(aminomethyl)aniline starting materials in toluene and catalysed by p-toluenesulfonic acid is developed. The 1 H-and 13 C-NMR spectra of the final products were assigned using a variety of one and two-dimensional NMR experiments. The distinction between the two potential isomers of the final products was made on the basis of heteronuclear multiple bond connectivity (HMBC) NMR spectra.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

et al. 2016

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Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

et al. 2020

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The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt half-chair and boat conformations, respectively. The absolute configuration was assigned on the the basis of L-proline, which was used in the synthesis of benzodiazepine. In the crystal, weak C—HBnz...ODiazp and C—HProprg...ODiazp (Bnz = benzene, Diazp = diazepine and Proprg = propargyl) hydrogen bonds link the molecules into two-dimensional networks parallel to the bc plane, enclosing R 4 4(28) ring motifs, with the networks forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.8%), H...C/C...H (25.7%) and H...O/O...H (20.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H...O hydrogen-bond energies are 38.8 (for C—HBnz...ODiazp) and 27.1 (for C—HProprg...ODiazp) kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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Racemic 9,10-dimethoxy-3-methyl-6-phenyl-7,7a-dihydrobenzo[b]benzo[4,5]isothiazolo[2,3-d][1,4]diazepine 12,12-dioxide

Cited by 2 publications

References 17 publications

Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

Synthesis and Spectral Characterization of Benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14H)-one Derivatives

Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

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