Synthesis of optically active 5,6,7,8-tetrahydroquinolines |
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Authors: | F. Soccolini G. Chelucci C. Botteghi |
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Affiliation: | Istituto di Chimica Applicata, Università di Sassari, Via Vienna, 2, 07100 Sassari, Italy |
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Abstract: | (+)-(R)-5-Methyl- and (+)-(R)-2,5-dimethyl-8-isopropylidene-5,6-dihydro-7H-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. |
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