Reinvestigation of the Nitration of Tri­chloroethene - Subsequent Reactions of the Products and Evaluation of Their Anti­microbial and Antifungal Activity

The nitration reaction of trichloroethene (1) to main products trichloronitroethene (TCNiE 2, up to 60.8 %, by GC), 1,1,2,2-tetrachloro-1-nitroethane (8, up to 25.1 %, by GC), and 1,2,2-trichloro-2-nitroethyl [chloro(nitro)methylene]azinate (9, up to 8.0 %, by GC) was comprehensively investigated and optimized. Different 1,1-diamino-2-chloro-2-nitroethenes, 2-nitroethoxyguanidines, and rare O-(1,2,2-trichloro-2-nitroethyl) oximes and carbimidoyl halides with unique formulas R–O–N=C(NO2)NRR1 and R–O–N=C(Hal)NRR1, respectively, were obtained from these nitration products in yields up to 91 %. The structure of (E)-morpholino(nitro)methanone O-(1,2,2-trichloro-2-nitroethyl) oxime (19) was proven by single-crystal X-ray diffraction analysis. In addition, the antimicrobial and antifungal activity of the synthesized compounds was examined. Notably, N-(1,2,2-trichloro-2-nitroethoxy)-3,4-dihydroisoquinoline-2(1H)carbimidoyl chloride (27) inhibited the growth of methicillin-resistant and sensitive Staphylococcus aureus with minimum inhibitory concentrations of 1.3 μg mL–1, and reduced the viability of the MCF-7 cancer cell line with an IC50 of 0.2 μg/mL.