title: Stable hemiaminals with a cyano group and a triazole ring.
abstract: Under neutral conditions the reactions between 4-amino-1,2,4-triazole and cyano-substituted benzaldehyde derivatives yield stable hemiaminals. Addition of small amounts of acid catalyst promotes further step of dehydration resulting in formation of Schiff bases. Four new hemiaminals and the corresponding imines have been obtained. The molecular stability of the hemiaminal intermediates results from both the 1,2,4-triazole moiety and electron withdrawing substituents on the phenyl ring, so no further stabilisation by intramolecular interaction is required. Hemiaminal molecules possess stereogenic centres on carbon and nitrogen atoms. The chirality of these centres is strongly correlated with the conformation of the molecules due to heteroatom hyperconjugation effects.
authors: Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, Wrocław 50-383, Poland. aniuta04@gmail.com.
authors: Anna
authors: A
authors: Kwiecień
authors: Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, Wrocław 50-383, Poland. barysiak@o2.pl.
authors: Maciej
authors: M
authors: Barys
authors: Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, Wrocław 50-383, Poland. ciunik@wchuwr.pl.
authors: Zbigniew
authors: Z
authors: Ciunik
mesh_terms: D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*
chemical_list: D012545:Schiff Bases; D014230:Triazoles; C533754:4-amino-1,2,4-triazole