L. Peyrot, M. Elkhatib, J. Vignalou
Jul 1, 2001
Citations
0
Influential Citations
7
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
1-Amino-2-methylindoline is a precursor used in the synthesis of antihypertension drugs. It reacts with monochloramine to lead to the formation of 1-amino-2-methylindole and azo(2-methyl)indoline. These new products have been isolated and characterized by microanalysis, uv, gc/ms, ir, and 1H/13C nmr. The reaction leads to the transient formation of an indolic aminonitrene. 1-Amino-2-methylindole formation proceeds in strongly alkaline medium by rearrangement of a diaziridine intermediate. In neutral or slightly alkaline medium, one obtains a precipitate of tetrazene type (-N-N=N-N-), the azo(2-methyl)indoline. The study of the thermochemical properties shows that tetrazene decomposes towards 150 °C to give the 1,1′-bi(2-methyl)indoline. The stability of the starting reagents and products was the subject of a systematic investigation. A reaction mechanism is proposed.