Steroidal Indoxyls, Indoles, and Quinolines

Alfred Hassner, Makhluf J. Haddadin, P. Catsoulacos

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


3β-Hydroxy-5-androsten-17-one (lb) was converted to a steroidal indoxyl IIb by a novel reaction with o-nitro-benzaldehyde. Other 17-keto steroids gave similar products. The proposed structure (II) is consistent with the chemical reactions of these compounds, and is corroborated by infrared, nmr, and ultraviolet spectra. The conversion of I to II proceeded via the aldol intermediate XI rather than via the o-nitrobenzal ketone V. The latter intermediate (V) provides another route to steroidal quinolines. A mechanism for the formation of II which involves intramolecular carbanion attack on a nitro group is proposed and discussed.

Original languageEnglish
Pages (from-to)1363-1369
Number of pages7
JournalJournal of Organic Chemistry
Issue number5
StatePublished - May 1966
Externally publishedYes


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