Chemoenzymatic Synthesis of Optically Active 2-Phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile

Chiral γ-Aryl-1H-1,2,4-triazole Derivatives as Highly Potential Antifungal Agents: Design, Synthesis, Structure, and in Vitro Fungicidal Activities

“…Fusarium oxysporium, Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Dothiorella gregaria, and Colletotrichum gossypii were provided through the courtesy of the Center for Bioassay, Central China Normal University. 1 H NMR and 13 C NMR spectra were recorded on a Mercury-Plus 400 spectrometer at 400 or 600 MHz, respectively. The chemical shifts are reported relative to CDCl 3 with TMS as the internal reference.…”

“…m, 1H), 3.40 (d, J ) 14.0 Hz, 1H), 3.48 (d, J ) 13.6 Hz, 1H), 3.78-3.81 (m, 1H), 7.18-7.21 (m, 3H), 7.26-7.29 (m, 2H) 13. C NMR (100 MHz, CDCl 3): δ 13.8, 19.7, 20.7, 22.4, 26.2, 29.2, 32.5, 35.9, 38.2, 41.4, 42.1, 44.3, 47.5, 48.1, 52.7, 64.9, 126.1, 127.4, 128.1, 143.8, 170.4.…”

“…White solid; mp 116-117°C; yield 87%. 1 H NMR (400 MHz, CDCl3): δ 0.81 (t, J ) 7.2 Hz, 3H), 0.96 (s, 3H), 1.15 (s, 3H), 1.05-1.39 (m, 6H), 1.54-1.63 (m, 2H), 1.85-1.89 (m, 3H), 2.0-2.01 (m, 2H), 3.0-3.03 (m, 2H), 3.18-3.20 (m, 1H), 3.41 (d, J ) 13.6 Hz, 1H), 3.49 (d, J ) 13.6 Hz, 1H), 3.77-3.80 (m, 1H), 7.14 (d, J ) 8.4 Hz, 2H), 7.24 (d, J ) 8.4 Hz, 2H) 13. C NMR (100 MHz, CDCl3): δ 13.8, 19.7, 20.6, 22.3, 26.2, 29.1, 32.5, 35.9, 38.2, 40.7, 41.9, 44.4, 47.5, 48.1, 52.7, 64.9, 128.2, 128.8, 131.6, 142.4, 170.0.…”

Biocatalysis Applied to the Synthesis of Agrochemicals

“…Systhane ® (8) (2-pchlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile) is commercially available for crop protection as a racemate with one quaternary chiral carbon. Im et al [42,43] reported a chemoenzymatic synthesis of optically active 2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl) hexanenitrile and 2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile in order to obtain the two enantiomers and compare their biological activities, (Fig. (8)).…”

Ru(II)‐PBTNNXN complex bearing functional 2‐(pyridin‐2‐yl)benzo[d]thiazole ligand catalyzed α‐alkylation of nitriles with alcohols

“…α ‐Alkylated nitriles represent important structural scaffold applied in versatile biomacromolecules, fine chemicals, and carboxylic acid derivatives . Conventional synthesis of α ‐alkylated nitriles with hazardous alkyl halides and strong bases often suffers from generating environmentally unfriendly byproducts .…”