Алкилирование енаминов, бета-дикетонов и енаминокетонов
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Organomet. Chem., 2000, 595, 308-312.
11. A. Tkachev, A. Rukavishnikov // Enaminones of the 2-acetylcyclopent-1- en-1-ylamine type derived from the terpenic compounds limonene, 3-carene and ?-cadinol. // Mendeleev Commun., 1992, 1, 161-162.
12. S. Popov, A. Tkachev // New chiral agents for resolution of racemic cis- permethric and cis-Z-cyhalothric acids. // Tetrahedron: Asymmetry, 1995,
6, 4, 1013-1018.
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14. A. Tkachev, S. Popov // Alkylation of enaminoketone with a modified carane skeleton. Formation of stable ?-diketone monoimines. // Russ. J.
Org. Chem., 1997, 33, 5, 601-606.
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Lett., 2000, 41, 1297-1301.
Приложение 1.
Данные и аннотации некоторых статей (Belstein Abstracts).
Alkylation of Enaminoketone with a Modified Carane Skeleton. Formation of
Stable (-Diketone Monoimines
A. V. Tkachev; S. A. Popov
Source details: Russ.J.Org.Chem. 1997, 33 : 5 601-606.
Document type: Journal
CODEN: RJOCEQ
Language: EN
CNR: 6090629
Original Source: Zh.Org.Khim. 1997, 33 : 5 660-665.
CODEN: ZORKAE
Language: RU
Abstract
Alkylation of a bicyclic enaminoketone, 1-((1R,5R)-3-amino-6,6- dimethylbicyclo[3.1.0]hex-2-en-2-yl))ethanone, with highly reactive alkyl halides (methyl iodide, benzyl halides, and allyl halides) in a two-phase system benzene-40% aqueous NaOH in the presence of benzyltriethylammonium chloride (BTEA) as phase-transfer catalyst results in formation of stable (- diketone monoimines, derivatives of the series of 1-((1R,5R)-2-alkyl-3- imino-6,6-dimethylbicyclo[3.1.0]hex-2-yl)ethanone, in 53-81% yields.
Alkylation of sterically hindered 1,3-diketones under phase-transfer conditions
A. S. Zanina; S. I. Shergina; I. E. Sokolov; M. S. Shvartsberg
Source details: Russ.Chem.Bl. 1996, 45 : 10 2389-2392.
Document type: Journal
CODEN: RCBUEY
Language: EN
CNR: 6056087
Original Source: Izv.Akad.Nauk Ser.Khim. 1996, 10 2518-2521.
CODEN: IASKEA
Language: RU
Abstract
Sterically hindered 1,3-diketones react selectively with propargyl and
allyl bromides under conditions of phase transfer catalysis to give C-
alkylated products, whereas reactions with butyl and benzyl chlorides yield
mixtures of C- and O-isomers.An increase in the size of the substituents
present in the initial 1,3-diketone hampers introduction of the second
propargyl group.The propargyl-substituted 1,3-diketones undergo cyclization
under the alkylation conditions to give substituted furans.
Sequence of alkylation of cyclohexane-1,3-dione. Alternative synthesis of
(+/-)-angustione
A. A. Zenyuk; L. G. Lis; L. I. Ukhova
Source details: Chem.Nat.Compd.(Engl.Transl.) 1991, 27 : 4
400-403.
Document type: Journal
CODEN: CHNCA8
Language: EN
CNR: 5645800
Original Source: Khim.Prir.Soedin. 1991, 4 460-463.
CODEN: KPSUAR
Language: RU
Abstract
A method is proposed for introducing one, two, or three alkyl substituents
into positions 4 and 6 of the cyclohexane-1,3-dione molecule by successive
alkylation under the action of strong bases. (+/-)-Angustione (a natural
-diketone) has been synthesized.
A Tandem Amino-Cope Rearrangement/Enamine Alkylation Reaction
Steven M. Allin; Martin A. C. Button; Stephen J. Shuttleworth
Source details: Syn.Lett. 1997, 6 725-727.
Document type: Journal
CODEN: SYNLES
Language: EN
CNR: 6086563
Abstract
Thermally induced (3,3)-sigmatropic rearrangement of 3-amino-1,5-diene substrates occurs to give the corresponding enamine products in high yield and with excellent trans:cis enamine selectivity.The enamine produced during the amino-Cope rearrangement has been directly derivatized, representing the first report of a tandem amino-Cope rearrangement/enamine alkylation reaction.The potential of this novel synthetic strategy is outlined.
N-alkylation of enaminones
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