Reaction of aminobenzoate esters with N,N′-dimethylformamide azine dihydrochloride: Crucial influence of intramolecular hydrogen bonding for the formation of 1,2,4-triazoles

Railliet, Antoine;Safin, Damir;Robeyns, Koen;Garcia, Yann
(2012) CrystEngComm — Vol. 14, n° 14, p. 4812-4818 (2012)

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Abstract
The reaction of N,N′-dimethylformamide azine (DMFA) or its dihydrochloride derivative (DMFA·2HCl) with o-RO(O)CC 6H 4NH 2 (R = Me, Et) leads to co-crystallization products o-RO(O)CC 6H 4NH 2·DMFA (R = Me, Et), while the same reaction of DMFA·2HCl with m- and p-RO(O)CC 6H 4NH 2 (R = Me, Et) provides the corresponding 4-substituted 1,2,4-triazoles (1-4). Reaction of the same m- and p-substituted amines with DMFA has failed, while addition of a few drops of HCl or HNO 3 in this reaction mixture has allowed us to obtain the corresponding triazole derivatives. Thus, the direct transamination reaction with the formation of triazoles 1-4 is catalysed by acidic catalysts. Molecular structures of DMFA, o-EtO(O)CC 6H 4NH 2·DMFA and 3 were elucidated by X-ray diffraction. © The Royal Society of Chemistry 2012.
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Railliet, A., Safin, D., Robeyns, K., & Garcia, Y. (2012). Reaction of aminobenzoate esters with N,N′-dimethylformamide azine dihydrochloride: Crucial influence of intramolecular hydrogen bonding for the formation of 1,2,4-triazoles. CrystEngComm, 14(14), 4812-4818. https://doi.org/10.1039/c2ce25095k (Original work published 2012)