An Isocyanide Based Three-component Reaction under Catalyst-free Conditions for Synthesis of New and Stable Trifluoromethylated Ketenimines and 1-Azabutadienes.

Ameri, Rosa Edris; Mohtat, Bita; Alipour, Eskandar; Mirza, Behrooz

In recent years, organofluorine compounds have achieved a significant place in life sciences.[1] Fluorinated compounds are prized because of their wide applications in medicinal chemistry and use in the modern chemical industry.[[2]] Among the fluorinated components, trifluoromethyl is one of the most important groups with many noteworthy applications in agrochemicals and pharmaceuticals.[6] In general, incorporation of the CF SB 3 sb group increases lipophilicity, solubility and the stability of the constituent compounds.[7] Trifluoromethylated compounds have shown such biological activities as antidepressant, anticancer, antimalarial, antihypertensive, antibacterial and antiviral properties.[8],[9] Combining CF SB 3 sb with N-H heterocyclic compounds has resulted in many applications.[10],[11] In order to optimize the reaction conditions (Table 1), we first examined the reaction of tert-butyl isocyanide B 1a b , ethyl 4,4,4-trifluorobutynoate B 2 b and 2-pyridinone B 3a b under catalyst and solvent-free conditions at 25 °C for 4h. The structures of B 4 b and B 5 b are obtained as pure products and have been confirmed by IR, SP 1 sp H NMR, [13]C NMR, [19]F NMR, mass spectroscopy and elemental analysis.

KETENIMINES; LIPOPHILICITY; BIOACTIVE compounds; SILICA gel; ORGANIC chemistry; ORGANIC synthesis; THIN layer chromatography

Organic Preparations & Procedures International, 2020, Vol 52, Issue 1, p37

0030-4948

Academic Journal

10.1080/00304948.2019.1694842