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Алкилирование енаминов, бета-дикетонов и енаминокетонов

    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-
 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.
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 ?-diketone monoimines. // Russ.  J.
    Org. Chem., 1997, 33, 5, 601-606.
15. T. Tiner-Harding, P. Mariano //  Intramolecular  photoarylations  of  N-
    (haloaryl)ethyl-?-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
   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

       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
 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
                    A. A. Zenyuk; L. G. Lis; L. I. Ukhova

 Source details:               Chem.Nat.Compd.(Engl.Transl.) 1991,  27  :  4
 Document type:              Journal
 CODEN:                        CHNCA8
 Language:                      EN
 CNR:                             5645800
 Original Source:            Khim.Prir.Soedin. 1991, 4 460-463.
 CODEN:                        KPSUAR
 Language:                     RU
 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


 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

                         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
 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


 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


  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

            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
  The  regioselectivity  of  the  C-alkylation   of   unsubstituted   N-aryl
enaminones prepared 
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Алкилирование енаминов, бета-дикетонов и енаминокетонов


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