Алкилирование енаминов, бета-дикетонов и енаминокетонов
ated
dimedone dimer. // J. Chem. Soc. Perkin Trans., 1981, 1, 3120-3124.
4. J. Whitesell, M. Whitesell // Alkylation of ketones and aldehydes via
their nitrogen derivatives. // Synthesis, 1983, 7, 517-536.
5. A. Zanina, S. Shergina, I. Sokolov, M. Shvartsberg // Alkylation of
sterically hindered 1,3-diketones under phase-transfer conditions. //
Russ. Chem. Bl., 1996, 45, 2389-2392 // Izv. Akad. Nauk Ser. Khim. 1996,
10, 2518-2521.
6. S. Lu, A. Lewin // Enamine-imine tautomerism in ?,?-unsaturated ?-amino
acids. // Tetrahedron, 1998, 54, 15097-15014.
7. J. Henriksen, S. Hammerum // Heats of formation of imine and enamine
radical cations and the corresponding neutral molecules // Int. J. Mass
Spect, 1998 179/180, 301-308.
8. S. Caccamese, G Principato // Resolution of the enantiomers of
tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via
an imine-enamine tautomerism. // Tetrahedron: Asymmetry, 1998, 9, 2939-
2945.
9. M. Shimizu, A. Morita, T. Kaga // Double nucleophilic addition to ?,?-
unsaturated aldimines induced by titanium tetrahalides. // Tetrahedron
Lett., 1999, 40, 8401-8405.
10. S. Knьppel, R. Frцlich, G. Erker // Formation of functionalized
[3]ferrocenophane derivatives by an enamine condensation reaction.// J.
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.
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carane skeleton. Formation of stable ?-diketone monoimines. // Russ. J.
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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
John V. Greenhill; Ashraf M. Moten
Source details: Tetrahedron 1983, 39 : 20 3405-3408.
Document type: Journal
CODEN: TETRAB
Language: EN
CNR: 5609239
Abstract
The base catalyzed N-alkylation of a series of primary and secondary
enaminones has been examined in detail.The enaminone anion was found to be
a weak nucleophile.Best results were obtained in tetrahydrofuran or dioxane
with sodium hydride and an alkyl iodide.
Alkylation of Ketones and Aldehydes via their Nitrogen Derivatives
James K. Whitesell; Marilyn A. Whitesell
Source details: Synthesis 1983, 7 517-536.
Document type: Journal
CODEN: SYNTBF
Language: EN
CNR: 5572282
Abstract
In this review, methods for the alkylation of the aldehydes and ketones
via formation of nitrogen derivatives such as enamines, metallated imines
(imine anions), metallated N,N-dialkylhydrazones (N,N-dialkylhydrazone
anions), dimetallated oximes (oxime dianions), and metallated O-
methyloximes (O-methyloxime anions) are described.Scope, limitations, and
advantages or disadvantages of the methods over comparative reactions of
enolates are also mentioned.
Intramolecular Photoarylations of N-(Haloaryl)ethyl ?-Enaminones
Tammy Tiner-Harding; Patrick S. Mariano
Source details: J.Org.Chem. 1982, 47 : 3 482-485.
Document type: Journal
CODEN: JOCEAH
Language: EN
CNR: 5570323
Abstract
The photochemistry of several N-(haloaryl)ethyl ?-enaminones was
investigated in order to develop methods for preparation of tricyclic
enaminone systems.The efficiencies of intramolecular photoarylations of the
haloaryl systems were found to be dependent upon the wavelength of
irradiation.Accordingly, irradiations of the haloaryl ?-enaminones 9a,c,d,f
with Pyrex-filtered light leads to formation of the reduced N-cyclized and
C-cyclized products 9b or 9e, 8a or 8b, and 10a or 10b, respectively. The
major products in these processes are the reduced materials.In contrast,
irradiations of the bromoaryl enaminones 9c or 9f with Vycor-filtered light
results in high yielding conversions to the C-cyclized tricyclic enaminones
10a and 10b in synthetically useful yields ranging from 50% to 85%.A
discussion of reasons for these wavelength dependencies is given in terms
of excited-state discrimination in these bichromophoric systems.Possible
reaction mechanisms are considered.The origin of another major product, 11,
generated by irradiation of 9f with Vycor-filtered light, is also
discussed.
Regioselective control of N-aryl enaminone alkylation
Denise Dugat; Daniel Gardette; Jean-Claude Gramain; Bertrand Perrin
Source details: Bull.Soc.Chim.Fr. 1994, 131 : 1 66-70.
Document type: Journal
CODEN: BSCFAS
Language: EN
CNR: 5851695
Abstract
The regioselectivity of the C-alkylation of unsubstituted N-aryl
enaminones prepared
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