One pot direct synthesis of amides or oxazolines from carboxylic acids using Deoxo-Fluor reagent

Abstract

A mild and highly efficient one pot-one step condensation and/or condensation-cyclization of various acids to amides and/or oxazolines using Deoxo-Fluor reagents is described. Parallel syntheses of various free fatty acids with 2-amino-2, 2-dimethyl-1-propanol resulted with excellent yields.

Figure 1

GC chromatograms of the reaction products of C16:0 (palmitic acid), C17:0 (heptadecanoic acid), C18:0 (stearic acid), C18:1 (oleic acid), and C18:2 (linoleic acid) with 2-amino-3-methyl-1-propanol, pyrrolidine, dimethyl amine and diethylamine, respectively. Conditions: GC-FID (Agilent GC-6890) the flow rate of carrier gas (He) was set at 5 mL/min. The oven temperature was programmed to initiate at 160 °C and held for 2 min. The temperature was raised to 200 °C at a rate of 20 °C and held for 4 min, and finally increased to 270 °C at a rate of 5 °C and held for 23 min. Column: SPD-1 fused-silica capillary column (30 m × 0.53 mm I.D., 0.10 μm film thickness; Supelco, Bellefonte, CA, USA). (a) Oxazolines derivatives; (b) pyrrolidine amide derivatives; (c) dimethyl amide derivatives; (d) diethyl amide derivatives.