Synthesis of N-(5-tetrazolyl)amidines from 5-aminotetrazole and nitriles using organoboranes

Perfluorinated pinacol promotes efficient amidination of 2-aminophenylboronic acid

“…Prior to our work, only one group had used organoboron compounds for the synthesis of amidines, this work was shown across two articles in 1987 and 1989. 4,5 In their first publication, Dorokhov et al described the synthesis of N-(5-tetrazolyl)amidines from 5-aminotetrazole through a borane-promoted amidination reaction (Scheme 2). 4 This reaction used an organoborane rather than the Pinner conditions due to the low basicity of the compound and the lower potential for side products.…”

“…4,5 In their first publication, Dorokhov et al described the synthesis of N-(5-tetrazolyl)amidines from 5-aminotetrazole through a borane-promoted amidination reaction (Scheme 2). 4 This reaction used an organoborane rather than the Pinner conditions due to the low basicity of the compound and the lower potential for side products. Scheme 2.…”