Химия /
confirmation by reduction of a dienaminone derivative of a dehydrated 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 α,β-unsaturated α-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 α,β-unsaturated aldimines induced by titanium tetrahalides. // Tetrahedron Lett., 1999, 40, 8401-8405.
10. S. Knüppel, R. Frölich, 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 δ-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.
13. J. Greenhill, A. Moten // N-Alkylation of enaminones. // Tetrahedron, 1983, 39, 3405-3408.
14. A. Tkachev, S. Popov // Alkylation of enaminoketone with a modified carane skeleton. Formation of stable β-diketone monoimines. // Russ. J. Org. Chem., 1997, 33, 5, 601-606.
15. T. Tiner-Harding, P. Mariano // Intramolecular photoarylations of N-(haloaryl)ethyl-β-enaminones. // J. Org. Chem., 1982, 47, 482-485.
16. P. Bugler, I. Cottrell, C. Cowden, A. Davies, U. Dolling // An investigation into the alkylation of 1,2,4-triazole // Tetrahedron 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
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 β-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 β-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 β-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