155222-86-9Relevant articles and documents
Preparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability
Chen, Yi-Hung,Ellwart, Mario,Toupalas, Georgios,Ebe, Yusuke,Knochel, Paul
supporting information, p. 4612 - 4616 (2017/04/13)
The treatment of various N-morpholino amides with TMPZnCl?LiCl (TMP=2,2,6,6-tetramethylpiperidyl) and Mg(OPiv)2 in THF at 25 °C provides solid zinc enolates with enhanced air and moisture stability (t1/2 in air: 1–3 h) after solvent evaporation. These enolates undergo Pd- and Cu-catalyzed cross-couplings with (hetero)aryl bromides as well as allylic and benzylic halides. The arylated N-morpholino amides were converted into various ketones by LaCl3?2 LiCl mediated acylation with Grignard reagents. The new, solid enolates were used to prepare a potent anti-breast-cancer drug candidate in six steps and 23 % overall yield.
Practical synthesis of amides from alkynyl bromides, amines, and water
Chen, Zheng-Wang,Jiang, Huan-Feng,Pan, Xiao-Yan,He, Zai-Jun
experimental part, p. 5920 - 5927 (2011/09/19)
A general and efficient method for the synthesis of a wide range of amides is described here. The reactions were conducted under convenient conditions and provided secondary and tertiary amides in moderate to excellent yields. A variety of amines and substituted alkynyl bromides were used to investigate the scope of the reactions.
A Study of the Ferrous Ion-initiated SRN1 Reactions of Halogenoarenes with tert-Butyl Acetate and N-Acylmorpholine Enolates
Leeuwen, Milko van,McKillop, Alexander
, p. 2433 - 2440 (2007/10/02)
A detailed preparative study is reported of the ferrous ion-initiated SRN1 reactions of a range of halogenoarenes with the sodium enolates of tert-butyl acetate, n-acetylmorpholine and a number of higher N-acylmorpholines.Smooth and rapid substitution occurs in many cases, and good to excellent yields were obtained of arylacetic esters or acids, arylacetamides and arylalkanamides.The broad scope and limitations of the process have been defined, and the possible role of the ferrous ion is discussed.
