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

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Railliet, Antoine [UCL] Safin, Damir [UCL] Robeyns, Koen [UCL] Garcia, Yann [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2012
Language Anglais
Journal information "CrystEngComm" - Vol. 14, no. 14, p. 4812-4818 (2012)
Peer reviewed yes
Publisher Royal Society of Chemistry
e-issn 1466-8033
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Links
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Bibliographic reference Railliet, Antoine ; Safin, Damir ; Robeyns, Koen ; Garcia, Yann. Reaction of aminobenzoate esters with N,N′-dimethylformamide azine dihydrochloride: Crucial influence of intramolecular hydrogen bonding for the formation of 1,2,4-triazoles. In: CrystEngComm, Vol. 14, no. 14, p. 4812-4818 (2012)
Permanent URL http://hdl.handle.net/2078.1/125501