Synthesis and spectral characterization of N-[2-(4-halophenoxy)-3-(3-chlorophenyl)-3, 4-dihydro-2H-1,3,2-λ5-benzoxazaphosphinin-2-yliden]-N-substituted amines by the Staudinger reaction

✍ Scribed by C. Venkateswarlu; P. V. V. Satyanarayana; C. V. Nageswara Rao; K. Reddy Mohan Naidu; C. Naga Raju

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 104 KB
• Volume: 21
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20639

✦ Synopsis

Abstract

The synthesis of the title compounds was accomplished in four steps. The synthetic route involves the preparation of Schiff's base by reacting salicylaldehyde with m‐chloroaniline in EtOH. The Schiff's base was then reduced with NaBH~4~/MeOH. In the second step, PCl~3~ was reacted with p‐chlorophenol/p‐bromophenol in THF in the presence of Et~3~N to obtain P(III) dichloride derivatives. The reduced Schiff's base and dichloride derivatives were reacted in equimolar quantities in the presence of Et~3~N in THF to get the cyclized product. Alkyl azides were prepared by reacting alkyl bromides with sodium azide, and then alkyl azides were treated with the cyclized product to obtain the title compounds. The structure of these novel compounds was elucidated by elemental analysis, IR, ^1^H, ^13^C, ^31^P NMR, and mass spectroscopy. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:499–504, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20639