in Wiley InterScience (www.interscience.wiley.com).Two distinct alternative methods using different starting materials for the preparation of dibenz [b,f] [1,4]oxazepine (7, CR) were reinvestigated. The possibility of trans-cis conversion of the Schiff base 5 (produced from 1 and 2) is considered the favorable orientation that leads to cyclization (production of 7). Fluoro derivative of 1 afforded excellent and more convenient conditions for the one pot preparation of high yield pure 7. The presence of only trans configuration for the imine 6 (produced from 3 with 4) and the impossibility of its conversion to cis, makes it inadequate for the preparation of 7.
The effect of temperature and catalyst on the yield and rate of the etherification reaction between 1 and 2 was investigated and alternative methods for separation of 3 and 4 from the reaction mixture have been described.
Cis-trans stereochemistry of 2-(2-chlorobenzylideneamino)phenol (1) and 2-(2-chlorophenyl imino)methyl)phenol (2) (Schiff bases) was studied by GC-MS spectrometry, and cis-trans conversion of the two compounds in solution was investigated by GC. Thus, 2 exists as a sole trans configuration and its conversion to cis was unsuccessful in any circumstance, while compound 1 exists as a mixture of two configurations in solution, occurrence of which were dependent on the temperature, heating time, solvent, and acid catalyst. X-ray crystallography of solid 1 presented a sole trans configuration.
Improved Etherification Procedure for the Preparation of Dibenz[b,f][1,4]oxazepine. -The effect of temperature and catalyst on yield and rate of the etherification reaction between (I) and (II) is studied and an alternative work-up procedure for the targeted dibenz[b,f][1,4]oxazepine (IV) (no yield given) is described. -(FAKHRAIAN*, H.; NAFARY, Y.; YARAHMADI, A.; HADJ-GHANBARY, H.; J.
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