Synthesis of [3-14C]- and [5-14C]-labelled 5-nitro-1,2,4-triazol-3-one (NTO) and study of its chemical decomposition

Autor:	Jean-Pierre Noël, Jamal Ouazzani, P. Varenne, S. de Suzzoni-Dezard, N. Robic, L. Le Campion, A. Vandais
Rok vydání:	1999
Předmět:	Organic Chemistry Biochemistry Medicinal chemistry Decomposition Analytical Chemistry chemistry.chemical_compound chemistry Drug Discovery Nitrosation Nitro Organic chemistry Radiology Nuclear Medicine and imaging Diazo Amine gas treating Azide Spectroscopy Chemical decomposition Bond cleavage
Zdroj:	Journal of Labelled Compounds and Radiopharmaceuticals. 42:1203-1213
ISSN:	1099-1344 0362-4803
Popis:	The chemical decomposition of NTO 1 and its corresponding amine ATO 2 was investigated. To make easier the identification of the decomposition products, we synthesized 14C-labelled NTO and ATO. Our results confirmed the high stability of the NTO triazolone ring. Its scission can be achieved partially by sulfuric acid under intensive heat and pressure. The triazolone ring of ATO was cleaved in alkaline solution. Carbon dioxide is evolved leaving a polar compound assumed to be aminoguanidine. The deamination of ATO was achieved by nitrosation. In dilute HCl (0.15N), 2 equivalents of NO−2 lead to the triazolone 4, through a radical de-diazotation of the diazo intermediate. With 3 to 10 equivalents of NO−2, the nitrosation leads exclusively to the azide 6. Copyright © 1999 John Wiley & Sons, Ltd.
Databáze:	OpenAIRE
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