Stable Hemiaminals with a Cyano Group and a Triazole Ring

Molecules

Anna Kwiecień¹  Maciej Barys² 

[1] Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, Wrocław 50-383, Poland;

关键词: stable hemiaminal;    stable intermediate;    heteroatom hyperconjugation;    crystal structure;    4-amino-1;    2;    4-triazole;    formylbenzonitrile;   

DOI  :  10.3390/molecules190811160

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.