Open AccessANNOTININE: THE REACTIONS OF THE CYCLIC ETHER FUNCTION
Author(s) -
Heinrich Meier,
P. Meister,
Léo Marion
Publication year - 1954
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v54-035
Subject(s) - chemistry , thionyl chloride , potassium permanganate , hydrate , lactone , oxime , reagent , chromic acid , medicinal chemistry , ether , organic chemistry , potassium , chloride
Treatment of annotinine chlorohydrin with chromous chloride has been found to produce not only the already reported unsaturated lactone A (C 16 H 21 O 2 N), but also a second unsaturated lactone B (C 16 H 21(23) O 2 N), and a hydroxylactone (C 16 H 23 O 3 N). Under the action of a concentrated solution of the same reagent the hydroxylactone is converted to the unsaturated lactone B. On hydrogenation the latter gives a dihydrolactone B which seems to contain a secondary amino group. Annotinine hydrate on treatment with thionyl chloride gives an unsaturated chlorolactone (C 16 H 20 O 2 NCl) which can be hydrogenated and subsequently dechlorinated to produce a third lactone C, different from either of dihydrolactones A or B, but which like the latter seems to contain an imino group. Oxidation of annotinine hydrate with chromic acid produces a hydroxyketone which can be converted into an oxime and, therefore, one of the hydroxyls of the hydrate is secondary while the other is probably tertiary. On the other hand, oxidation of annotinine with potassium permanganate gives rise to a lactam which by the Clemmensen reduction is converted to a mixture of lactam chlorohydrin and dihydrolactone A.