863329-50-4Relevant academic research and scientific papers
Aromatization and ring cyclization: A better understanding on the ring cyclization mechanism of 3-amino-6-hydrazino-1,2,4-triazin-5(2H)-one reacted with acetic acid in N,N-dimethylformamide
Hwang, Long-Chih,Wu, Rang-Rong,Tu, Chun-Hsien
, p. 851 - 855 (2005)
In this paper we report that the title compound (3) reacts with excess N,N-dimethylformamide (DMF) containing two equivalents of acetic acid to afford 6-amino-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-one (1). When 3-amino-2-benzyl-6-hydrazino-1,2,4-triazin-5(2H)-one (6), the N-2 benzylated derivative of 3, is treated under the same conditions, ring Cyclization does not occur; instead, 3-amino-2-benzyl-6-(2-formyl-hydrazino)-1,2,4-triazin-5(2H)-one (7) is formed. Single-crystal X-ray analysis of a 3-ethyl derivative of compound 1 reveals the predominant tautomeric structure to be the 7H-tautomer (7H-1). From these results, we propose a reasonable cyclization mechanism that incorporates two important points: (1) the tautomerism of the N-2 hydrogen with the C-5 oxo group aromatizes the 1,2,4-triazine ring, and (2) the DMF is protonated by acetic acid on the nitrogen atom, then deamination occurs where DMF is attacked by the 6-hydrazino group of 3 or 6.
Aromatization and ring cyclization: A reasonable understanding on the ring cyclization mechanism of 3-amino-6-hydrazino-1,2,4-triazin-5(2H)-one reacted with one-carbon fragment reagents or nitrous acid
Hwang, Long-Chih,Tu, Chun-Hsien,Wang, Jung-Hui
, p. 889 - 895 (2006)
The cyclization mechanism for the title compound (2) reacting with one-carbon fragment reagents or nitrous acid to afford heterobicyclic compounds 6-amino-3-substituted-1,2,4-triazolo[3,4-f][1,2,4]triazin-8(7H)-ones (3a-d) or 6-amino-1,2,3,4-tetrazolo[5,1
