TY - JOUR
T1 - Steroidal Indoxyls, Indoles, and Quinolines
AU - Hassner, Alfred
AU - Haddadin, Makhluf J.
AU - Catsoulacos, P.
PY - 1966/5
Y1 - 1966/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=33947332919&partnerID=8YFLogxK
U2 - 10.1021/jo01343a013
DO - 10.1021/jo01343a013
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AN - SCOPUS:33947332919
SN - 0022-3263
VL - 31
SP - 1363
EP - 1369
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -