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Synthesis of [3‐ 14 C]‐ and [5‐ 14 C]‐labelled 5‐nitro‐1,2,4‐triazol‐3‐one (NTO) and study of its chemical decomposition
Author(s) -
Le Campion L.,
de SuzzoniDezard S.,
Robic N.,
Vandais A.,
Varenne P.,
Noel J. P.,
Ouazzani J.
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199912)42:12<1203::aid-jlcr276>3.0.co;2-f
Subject(s) - chemistry , nitrosation , deamination , diazo , decomposition , amine gas treating , nitro , ring (chemistry) , sulfuric acid , medicinal chemistry , nitrous acid , chemical decomposition , organic chemistry , azide , alkyl , enzyme
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 14 C‐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.