2-Aminoindoles
1971; Elsevier BV; Volume: 27; Issue: 4 Linguagem: Inglês
10.1016/s0040-4020(01)92472-x
ISSN1464-5416
AutoresTohru Hino, M. NAKAGAWA, Tomohiro Hashizume, N. YAMAJI, Yasuhiko Miwa, K. Tsuneoka, Sanya Akaboshi,
Tópico(s)Organic Chemistry Cycloaddition Reactions
Resumo2-Aminoindoles (2 and 4) have been prepared by the reaction of 2-indolinethiones (1) with primary and secondary aliphatic amines. The reaction of 1b with ethyleneimine produced the S-alkylated product 5, and with phenylhydrazine compound 9. The reaction 1b with aniline and 10 with piperidine failed to give an 2-aminoindole derivative or 12. The UV and NMR spectra of the free base 2 shows the presence of a tautomeric mixture of 13 and 14 in bases 2c, 2g, 2h and 2i. The free base 2b in CDCl3 exists substantially in the indolenine form 15. The free bases of 2b, 2g, 2h and 2i are susceptible to autoxidation to 3-oxo derivatives (19, 21, 22 and 23).
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