Synthesis, infrared spectral studies and theoretical calculations of 4-phenyl-4,5-dihydrobenzo[<i>f</i>][1,4]oxazepin-3(2<i>H</i>)-one (thione)
JOURNAL OF MOLECULAR STRUCTURE, vol.892, no.1-3, pp.132-139, 2008 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 892 Issue: 1-3
- Publication Date: 2008
- Doi Number: 10.1016/j.molstruc.2008.05.023
- Journal Name: JOURNAL OF MOLECULAR STRUCTURE
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.132-139
- Kocaeli University Affiliated: Yes
Abstract
Salicylaldehyde (1) was reacted with aniline to afford 2-[(E)-(phenylimino)methyl]phenol (2). The reduction of (2) by NaBH4 gave 2-((phenylamino)methyl)phenol (3) which was reacted with chloroacetyl chloride to give 2-chloro-N-(2-hydroxybenzyl)-N-phenylacetamide (4). Compound (4) was cyclized to 4-phenyl-4.5-dihydrobenzo[f][4]oxazepin-3(2H)-one (5) by NaOH in ethanol solution. The treatment of compound (5) with P2S5 gave corresponding 4-phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thione (6). The structures of (5) and (6) were determined by H-1 NMR and IR spectra. The optimized structural parameters and vibrational frequencies of (5) and (6) were calculated by DFT with 6-31G(d,p) basis set. The mechanism of the cyclization reaction was studied by RHF with the standard 3-21G basis set. (C) 2008 Elsevier B.V. All rights reserved.