5 years ago

Solid State Separation and Isolation of Tautomers of Fused-Ring Triazolotriazoles

Solid State Separation and Isolation of Tautomers of Fused-Ring Triazolotriazoles
Andrea Peluso, Carla Manfredi, Sabato Volino, Amedeo Capobianco, Roberto Centore, Sandra Fusco, Antonio Carella, Maria Vittoria Ferrara
Fine control of the tautomeric forms of [1,2,4]triazolo[3,2-c][1,2,4]triazole derivatives in acidic conditions has been achieved by acting on the electronic character of the substituent at position 7 of the heterobicycle and on the counterion. Strong electron releasing or electron withdrawing substituents lead almost exclusively to a single tautomeric form, the 1H-3H or the 2H-3H, respectively. In the case of the phenol substituent, both tautomeric forms are present in comparable amount in solution; the two tautomers can also be selectively precipitated in different crystalline salts using suitable counterions.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00380

DOI: 10.1021/acs.joc.7b00380

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