1971-49-9Relevant articles and documents
Synthesis of N,O-acetals by net amide C[sbnd]N bond insertion of aldehydes into N-acyl phthalimides and N-acyl azoles
Enright, Robert N.,Grinde, Jeffrey L.,Wurtz, Lincoln I.,Paeth, Matthew S.,Wittman, Tekoa R.,Cliff, Emily R.,Sankari, Yessra T.,Henningsen, Lucas T.,Tan, Chuchen,Scanlon, Joseph D.,Willoughby, Patrick H.
, p. 6397 - 6408 (2016/09/23)
We found that N-acyl phthalimides and several N-acylated azoles are capable of reacting with aldehydes to form O-acyl-N,O-acetals in an apparent amide C[sbnd]N bond insertion. In the context of N-acyl phthalimides, the reaction is mediated by substoichiometric amounts of sodium iodide and potassium phthalimide. DFT computations supported a proposed mechanism and provided insights into the effect of the alkali metal additive. This strategy could be used to prepare a myriad of N,O-acetals from a range of aldehydes. A one-pot procedure was also developed in which N-acyl phthalimide was generated in situ prior to forming the N,O-acetal product. The one-pot strategy was used to demonstrate that activated amides derived from imidazole, pyrazole, (benzo)triazole, and tetrazole are also amenable substrates. Collectively, these studies provide an approach to the synthesis of a variety of N,O-acetals under mild conditions from inexpensive starting materials.
Synthesis and evaluation of some variants of the Nefkens' reagent
Goodman, Cassie A.,Hamaker, Christopher G.,Hitchcock, Shawn R.
supporting information, p. 6012 - 6014 (2013/10/22)
A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3) 3] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction.
REAGENTS AND SYNTHETIC METHODS. 29. N-ACYLPHTHALIMIDES FROM CARBOXYLIC ACIDS AND PHOSPHOROUS REAGENTS UNDER PHASE TRANSFER CONDITIONS
Lago, J. M.,Palomo, C.
, p. 653 - 658 (2007/10/02)
N-acylphthalimides are obtained from carboxylic acids and potassium phthalimide by means of phenyl dichlorophosphoridate or diphenylphosphorophthalimide under phase transfer conditions.