Synthesis and characterization of new heterocyclic derivatives by oxidation of 1-amino-2-methylindoline

Citation
L. Peyrot et al., Synthesis and characterization of new heterocyclic derivatives by oxidation of 1-amino-2-methylindoline, J HETERO CH, 38(4), 2001, pp. 885-893
Citations number
23
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
4
Year of publication
2001
Pages
885 - 893
Database
ISI
SICI code
0022-152X(200107/08)38:4<885:SACONH>2.0.ZU;2-1
Abstract
1-Amino-2-methylindoline is a precursor used in the synthesis of antihypert ension drugs. It reacts with monochloramine to lead to the formation of 1-a mino-2-methylindole and azo(2-methyl)indoline. These new products have been isolated and characterized by microanalysis, uv, gc/ms, ir, and H-1/C-13 n mr. The reaction leads to the transient formation of an indolic aminonitren e. 1-Amino-2-methylindole formation proceeds in strongly alkaline medium by rearrangement of a diaziridine intermediate. In neutral or slightly alkali ne 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 t etrazene decomposes towards 150 degreesC to give the 1,1'-bi(2-methyl)indol ine. The stability of the starting reagents and products was the subject of a systematic investigation. A reaction mechanism is proposed.