73894-67-4Relevant academic research and scientific papers
Acid-catalysed, Nucleophile-catalysed and Thermal Decomposition of 2-Amino-3-(2',2'-dimethylaziridino)-1,4-naphthoquinone
Antonini, Ippolito,Claudi, Francesco,Cristalli, Gloria,Grifantini, Mario,Martelli, Sante
, p. 181 - 185 (2007/10/02)
The course of the thermal, acid-catalysed and iodide-catalysed decomposition of 2-amino-3-(2',2'-dimethylaziridino)-1,4-naphthoquinone (III) was investigated.Thermal and iodide-catalysed decompositions gave mainly 2,3-diamino-1,4-naphthoquinone (VI) and 2-amino-3-(2'-methylallylamino)-1,4-naphthoquinone (V) together with low amounts of 2,2-dimethyl-1,2,3,4,5,10-hexahydrobenzoquinoxaline (IV) and 2-isopropyl-1H-naphthoimidazole-4,9-dione (VII).The acid catalysed isomerization of the aziridinonaphthoquinone III with halohydric acids or with acetic acid readily gave the opening of the aziridine ring; the corresponding salts of 2-amino-3-(2'-haloisobutylamino)-1,4-naphthoquinones (VIIIa-c) and 2-amino-3-(2'-acetoxyisobutylamino)-1,4-naphthoquinone (X) were formed by cleavage of the carbon-nitrogen bond at the substituted carbon atom.Hypotheses on the mechanism of these reactions are given.
