N-[1-(Benzotriazol-1-yl)alkyl]amides, versatile amidoalkylation reagents. 5. A general and convenient route to N-(.alpha.-alkoxyalkyl)amides

Comparative Studies on the Amidoalkylating Properties of N-(1-Methoxyalkyl)Amides and 1-(N-Acylamino)Alkyltriphenylphosphonium Salts in the Michaelis–Arbuzov-Like Reaction: A New One-Pot Transformation of N-(1-Methoxyalkyl)Amides into Phosphonic or Phosphinic Analogs of N-Acyl-α-Amino Acids

“…The final reaction mixture also contained the starting N-(1-methoxyethyl)amide 5a (11%), phosphonium salt 6a (10%), methanol (63%), triphenylphosphine (11%), methyltriphenylphosphonium tetrafluoroborate (82%), starting trimethylphosphite (28%), and, unexpectedly, dimethylphosphite (10%). Very similar results were obtained in a reaction of amide 5a with triethylphosphite (entries [16][17].…”

“…[4][5][6][7][8][9][10][11][12][13] The limitations and disadvantages of most of the above-mentioned amidoalkylating agents were reviewed by Katritzky et al 4,[14][15][16][17] Many of them (X = OR, Cl, Br) are relatively unstable compounds that cannot be stored for a prolonged period of time and thus have to be prepared in situ. Preparation of some of these amidoalkylating agents (X = Cl, Br) is relatively difficult or labor-consuming.…”

“…Most of them (X = OH, NHCOR, or 1-benzotriazolyl), including the most frequently used α-alkoxy derivatives (X = OR), require activation with Lewis acids, which are often quite expensive (e.g., ZrCl 4 , VCl 3 , CeCl 3 , or InCl 3 ). 4,[13][14][15][16][17] Application of Lewis acid has also been shown to diminish the activity of a reacting nucleophile and also necessitates a labor-consuming aqueous work-up procedure, which usually destroys the catalyst.…”

Study of the Reactions of Fluorine‐Containing Amides with Aldehydes and the Structures of the Bisamides

“…4 Their preparation has drawn much attention, and many synthetic methods have been reported. [5][6][7] Usually symmetrical 1,1-bisamides were prepared by the direct reaction of aldehydes with the corresponding amides using a strong acid catalyst, e.g. sulfuric acid, sulfonic acid or hydrochloric acid, at high temperature.…”

XtalFluor-E® mediated proto-functionalization of N-vinyl amides: access to N-acetyl N,O-acetals

“…These include condensation of aldehydes with amides in the presence of titanium ethoxide, 9 benzotriazole 10, 11 or sodium benzenesulfinate, 12 as well as the reduction of nitriles with Schwartz reagent followed by the reaction of the resulting intermediate with acyl chloride and alcohol. 13 Szymura and coworkers used the Hofer-Moest reaction for the electrochemical decarboxylative methoxylation of N -acteyl-α-amino acids to generate N -(α-methoxyalklyl)-amides.…”