Amino-nitrile cleavage in the electrochemical reduction of hydeazones of aromatic aldehydes

Unexpected Cleavage of N‐N Bonds of Pentafluorophenylhydrazones – Formation of Nitriles by a Radical Fragmentation Reaction

“…Creary described in detail the radical S RN 1 reactions of arylhalodiazirines with the azide ion, which also yielded the corresponding nitriles . The amino‐nitrile cleavage (ANC) reaction, known for decades, also yields nitriles from corresponding aromatic hydrazones – the reaction proceeds under different reaction conditions or is performed as an electrochemical reaction in an electrochemical cell only . The literature references were inspiring in proposing possible reaction mechanisms and structures of reaction intermediates for the DFT calculation of spin densities for EPR spin simulation, but our efforts were not successful.…”

“…[13] The amino-nitrile cleavage (ANC) reaction, known for decades, also yields nitriles from corresponding aromatic hydrazones -the reaction proceeds under different reaction conditions or is performed as an electrochemical reaction in an electrochemical cell only. [14] The literature references were inspiring in propos-Scheme 3. The reaction of the substrate 3 a with NaN 3 and NaCN offered the same reaction products.…”

N-[4-(Dimethylamino)benzylidene]-4H-1,2,4-triazol-4-amine

“…Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. (Desenko et al, 1995;Kargin et al, 1988;Modzelewska & Kalabun, 1999). In recent years, various 1,2,4-triazoles and their derivatives have been found to be associated with diverse pharmacological activities such as anticonvulsant, antifungal, anticancer, anti-inflammatory and antibacterial (Rollas et al, 1993;Todoulou et al, 1994).…”

“…For the biological activity of triazole derivatives, see: Modzelewska & Kalabun (1999); Rollas et al (1993); Todoulou et al (1994); Demirbas et al (2002); Kahveci et al (2003). For 4-amino-1,2,4-triazole Schiff bases, see: Desenko & Khim (1995); Kargin et al (1988).…”

4-(4-Hydroxybenzylideneamino)-4H-1,2,4-triazole hemihydrate

“…The aroyl Schiff bases of 4-amino-1,2,4-triazole have received considerable attention over the past few decades (Kitaev et al, 1971;Mazza et al, 1976;Kargin et al, 1988). It is of interest that some of them are anti-in¯ammatory agents (Gupta & Bhargava, 1978) and new coccidiostatic drugs (Colautti et al, 1971).…”