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Note | Regular issue | Vol 65, No. 8, 2005, pp.1939-1946
Published online, 27th May, 2005
DOI: 10.3987/COM-05-10401
■ 5H-[1,2,5]Selenadiazolo[3,4-f]indole as a Masked Form of 5,6-Diaminoindole

Jealux Okwakol and Spiros Grivas*

*Department of Biosciences, Karolinska Institutet, Södertörn University College, Novum Research Park, SE-141 57 Huddinge, Sweden

Abstract

6-Nitroindoline (9) was converted into 1-acetyl-5,6-aminoindoline (12) which was then transformed via selenadiazoles (13–15) to the title selenadiazoloindole (4) by two alternative 3-step synthetic sequences in 38–42% overall yield from 12. The unstable 5,6-diaminoindole (16) was then obtained by reductive deselenation of 4. Fully assigned 1H, 13C and 77Se NMR spectral data for the title indole (4) and 77Se NMR spectral data for the intermediate selenadiazoles (13–15) are presented.