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Synthesis of optically active 5,6,7,8‐tetrahydroquinolines
Author(s) -
Soccolini F.,
Chelucci G.,
Botteghi C.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210414
Subject(s) - chemistry , methyl vinyl ketone , ketone , enamine , acrolein , ether , adduct , hydrochloride , oxime , pulegone , organic chemistry , catalysis , chromatography , essential oil
(+)‐( R )‐5‐Methyl‐ and (+)‐( R )‐2,5‐dimethyl‐8‐isopropylidene‐5,6‐dihydro‐7 H ‐quinoline, 7 and 11 , were synthesized by reaction of ( R )‐pulegon morpholino‐enamine with acrolein or methyl vinyl ketone. The Michael adducts thus formed were reacted with hydroxylammonium hydrochloride in polar media. Compound 7 was also obtained by thermal rearrangement of the O ‐allyl ether of pulegone oxime. The selectivity of both synthetic methods were rather poor (30–49%). Isolation of 7 and 11 in the pure state was accomplished by preparative glc.