918655-33-1Relevant academic research and scientific papers
A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
Balkrishna, Shah Jaimin,Kumar, Sangit
, p. 1417 - 1426 (2012/06/30)
An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
Synthesis of olefinic crown diamides and their conversion into pyrazolino macrocycles: Promising photoluminescent crown compounds
Malhas, Rana N.,Ibrahim, Yehia A.
, p. 3261 - 3269 (2008/09/17)
Macrocyclic crown diamides with 16- or 24-membered rings containing E- and Z-olefinic double bonds were synthesized either by bisalkylation or by ring-closing metathesis (RCM) techniques. The two methods were evaluated and compared with regard to yield and to product stereochemistry. Isomerization of some Z-olefinic macrocycles to their corresponding E-isomers was achieved using Grubbs' catalyst second generation. Some of the required starting dials, diols and bishalo compounds were prepared by different routes including cross-metathesis (CM). The latter was compared with other investigated methods. Some of the olefinic macrocycles were subjected to cycloaddition reactions with diphenylnitrileimine to give the corresponding pyrazolino macrocycles. The latter showed interesting emission spectra. Georg Thieme Verlag Stuttgart.
