187875-01-0Relevant articles and documents
Synthesis, reactions and theoretical studied of triazolotriazolopyrazinium-3-aminides
Crabb, Derek L.,Main, David A.,Morley, John O.,Preston, Peter N.,Wright, Stanley H. B.
, p. 49 - 58 (2007/10/03)
Triazolopyrimidinium-3-aminides 5a-h have been synthesised by treatment pyridin-6-yl thiosemicarbazide derivatives 7f-n with dicyclohexylcarbodiimide (DCC).The above aminides 5a-h were slowly hydrolysed in water but very rapidly hydrolysed in 5 M aqueous hydrochloric acid to give substituted 1,2,4-triazole derivatives (e.g. 5a,d,g -> 8e,a,f, respectively); related nucleophilic ring-opening reactions occurred when the aminides (cf. 5a-h) were treated with (separately) methanol and ethanol (e.g. 5d->8c and 8d, respectively).A series of analogous triazolopyrazinium-3-aminides 6a-e was prepared following the procedures described above.The pyrazinium aminides 6 are stable in aq. 2 M HCl, and a stable hydrochloride salt 13 was formed from one such substrate 6a.