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Title: Stereochemistry of N<sub>5</sub>‑acyltetrahydro‑1,5‑benzodiazepines – NMR spectra and semiempirical MO calculations
Authors: Venkatraj, M
Jeyaraman, R
Ponnuswamy, S
Keywords: N<sub>5</sub>‑Acyltetrahydro-1,5-benzodiazepine
NMR spectra
Semiempirical MO calculation
boat conformation
X‑ray crystal structure
Issue Date: Jun-2006
Publisher: CSIR
Series/Report no.: <b>Int.Cl.<sup>8</sup> C07D</b>
Abstract: The conformational preferences of N<sub>5</sub>‑acyltetrahydro-1,5-benzodiazepines <b style="">3-5</b> have<b style=""> </b>been studied using NMR spectral techniques and semiempirical MO calculations (AM1 and PM3 methods). The N<sub>5</sub>‑formyl‑, N<sub>5</sub>‑acetyl‑ and N<sub>5</sub>‑benzoyl­tetrahydro‑2‑methyl‑2,4‑diphenyl ‑1<i style="">H-</i>1,5 benzodiazepines <b style="">3-5</b> prefer boat conformations <b style="">BE</b> with exo orientation of the acyl groups at N5. The X‑ray crystal structure of N<sub>5</sub>‑acetyl<b style=""> </b>derivative<b style=""> 4</b> also shows a boat conformation <b style="">BE</b> with <i style="">exo </i>orientation of acetyl group at N5. The results obtained from semiempirical MO calculations (AM1 and PM3) are in excellent agreement with the results obtained from solution and solid states.
Description: 1531-1540
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(06) [June 2006]

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