56384-34-0Relevant articles and documents
Tungsten-Catalyzed Transamidation of Tertiary Alkyl Amides
Feng, Fang-Fang,Liu, Xuan-Yu,Cheung, Chi Wai,Ma, Jun-An
, p. 7070 - 7079 (2021/06/30)
Transamidation has recently emerged as a straightforward and convenient means to diversify amides. However, the kinetically and thermodynamically demanding transamidation of notoriously robust, fully alkyl-substituted tertiary amides still remains a longstanding challenge. Here, we describe a method for the activation of tertiary alkyl amides to streamline transamidation using simple tungsten(VI) chloride as a catalyst and chlorotrimethylsilane as an additive. The highly electrophilic and oxophilic tungsten catalyst enables the selective scission of a C-N bond of tertiary alkyl amides to effect transamidation of a myriad of structurally and electronically diverse tertiary alkyl amides and amines. Mechanistic study implies that the synergistic effect of the catalyst and the additive could pronouncedly induce the nucleophilic acyl substitution of tertiary alkyl amide with amine to realize transamidation.
Intramolecular Vilsmeier processes: a new route to cyclopenta- and cyclohexa-fused quinolines by cyclisation of adipic and pimelic bis-amides
Meth-Cohn, Otto,Goon, Simon
, p. 85 - 90 (2007/10/03)
Symmetrical and unsymmetrical bis-amides derived from adipic and pimelic acid and secondary amines react in POCl3 solution to give the title compounds by way of a Vilsmeier reagent-α-chloro enamine interaction.Adipanilide and pimelanilide only cyclise with added PCl5.However the bis-N-substituted derivatives (N-methyl or N-phenyl) of adipanilide and pimelanilide give quinolinium salts in good yield.Unsymmetrical amides with an N-substituted anilide at one end and an aliphatic unit at the other only proceed as far as the intermediate stage, giving 1,2-disubstituted cyclo-pentanes or -hexanes.Analogous amides derived from suberic and sebacic acid do not give quinolinium salts but instead give complex mixtures.
