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Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one

Maria Aleksandrovna Galkina 1
Maria Aleksandrovna Galkina
, 
Georgy Vladimirovich Bodrin 1
Georgy Vladimirovich Bodrin
, 
Evgenii Iosifovich Goryunov 1
Evgenii Iosifovich Goryunov
, 
Irina Borisovna Goryunova 1
Irina Borisovna Goryunova
, 
Aleksandra Sergeevna Sherstneva 1
Aleksandra Sergeevna Sherstneva
, 
Jumakan Samybekovna Urmambetova 1
Jumakan Samybekovna Urmambetova
, 
Natal'ya Georgievna Kolotyrkina 2
Natal'ya Georgievna Kolotyrkina
, 
Mikhail Mikhailovich Il'in 1
Mikhail Mikhailovich Il'in
,  , 
Konstantin Aleksandrovich Kochetkov 1
Konstantin Aleksandrovich Kochetkov
10.1016/j.mencom.2016.01.029
Published 2015-12-30
Communication , Volume 26, Issue 1, 75-76
6
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Galkina M. A. et al. Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one // Mendeleev Communications. 2015. Vol. 26. No. 1. pp. 75-76.
GOST all authors (up to 50) Copy
Galkina M. A., Bodrin G. V., Goryunov E. I., Goryunova I. B., Sherstneva A. S., Urmambetova J. S., Kolotyrkina N. G., Il'in M. M., Brel V. K., Kochetkov K. A. Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one // Mendeleev Communications. 2015. Vol. 26. No. 1. pp. 75-76.
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TY - JOUR
DO - 10.1016/j.mencom.2016.01.029
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.029
TI - Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one
T2 - Mendeleev Communications
AU - Galkina, Maria Aleksandrovna
AU - Bodrin, Georgy Vladimirovich
AU - Goryunov, Evgenii Iosifovich
AU - Goryunova, Irina Borisovna
AU - Sherstneva, Aleksandra Sergeevna
AU - Urmambetova, Jumakan Samybekovna
AU - Kolotyrkina, Natal'ya Georgievna
AU - Il'in, Mikhail Mikhailovich
AU - Brel, Valery Kuzmich
AU - Kochetkov, Konstantin Aleksandrovich
PY - 2015
DA - 2015/12/30
PB - Mendeleev Communications
SP - 75-76
IS - 1
VL - 26
ER -
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@article{2015_Galkina,
author = {Maria Aleksandrovna Galkina and Georgy Vladimirovich Bodrin and Evgenii Iosifovich Goryunov and Irina Borisovna Goryunova and Aleksandra Sergeevna Sherstneva and Jumakan Samybekovna Urmambetova and Natal'ya Georgievna Kolotyrkina and Mikhail Mikhailovich Il'in and Valery Kuzmich Brel and Konstantin Aleksandrovich Kochetkov},
title = {Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one},
journal = {Mendeleev Communications},
year = {2015},
volume = {26},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.029},
number = {1},
pages = {75--76},
doi = {10.1016/j.mencom.2016.01.029}
}
MLA
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MLA Copy
Galkina, Maria Aleksandrovna, et al. “Regioselective aza-Michael addition of azoles to 4-(diphenylphosphoryl)but-3-en-2-one.” Mendeleev Communications, vol. 26, no. 1, Dec. 2015, pp. 75-76. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.029.

Abstract

Aza-Michael reaction of (E)-4-(diphenylphosphoryl)but-3-en-2-one with mono- and bicyclic nitrogen heterocycles proceeds regioselectively in the absence of catalysts to give the corresponding ß-diphenylphosphoryl-b-azahetarylalkanones. Its reaction with imidazole in the presence of chiral organocatalysts affords the corresponding enantiomerically enriched adduct in higher yield.

References

2.
10.1016/j.mencom.2016.01.029_bib0010
Xu
Chin. J. Org. Chem., 2005
3.
Asymmetric Enamine Catalysis
Mukherjee S., Yang J.W., Hoffmann S., List B.
Chemical Reviews, 2007
4.
Organocatalytic asymmetric conjugate additions
Almaşi D., Alonso D.A., Nájera C.
Tetrahedron Asymmetry, 2007
5.
10.1016/j.mencom.2016.01.029_bib0020
Luo
Synthesis, 2009
8.
10.1016/j.mencom.2016.01.029_bib0035
Bayindir
Synlett, 2010
9.
The Phospha‐Michael Addition in Organic Synthesis
Enders D., Saint‐Dizier A., Lannou M., Lenzen A.
European Journal of Organic Chemistry, 2005
10.
A study on the michael addition of dialkylphosphites to methylvinylketone
Keglevich G., Sipos M., Takács D., Greiner I.
Heteroatom Chemistry, 2007
14.
Synthesis of β-Aminophosphonates and -Phosphinates
Palacios F., Alonso C., de los Santos J.M.
Chemical Reviews, 2005
15.
Studies on Novel Bone Resorption Inhibitors. II. Synthesis and Pharmacological Activities of Fused Aza-heteroarylbisphosphonate Derivatives.
TAKEUCHI M., SAKAMOTO S., KAWAMUKI K., KURIHARA H., NAKAHARA H., ISOMURA Y.
Chemical and Pharmaceutical Bulletin, 2011
16.
Acyl phosphonates: good hydrogen bond acceptors and ester/amide equivalents in asymmetric organocatalysis.
Jiang H., Paixão M.W., Monge D., Jørgensen K.A.
Journal of the American Chemical Society, 2010
17.
Zagidullin A.A., Bezkishko I.A., Miluykov V.A., Sinyashin O.G.
Mendeleev Communications, 2013
19.
Artem’ev A.V., Gusarova N.K., Malysheva S.F., Belogorlova N.A., Kazheva O.N., Alexandrov G.G., Dyachenko O.A., Trofimov B.A.
Mendeleev Communications, 2015
20.
10.1016/j.mencom.2016.01.029_sbref0065a
Tarasova
Butlerovskie Soobshcheniya, 1999
21.
10.1016/j.mencom.2016.01.029_sbref0065b
Tarasova
Butlerovskie Soobshcheniya, 1999
22.
[DIALKYLCARBAMOYLMETHYL] PHOSPHINE OXIDES ON THEIR EXTRACTION CAPACITY AND SELECTIVITY
Myasoedov B.F., Chmutova M.K., Kochetkova N.E., Koiro O.E., Pribylova G.A., Neeterova N.P., Medved T.Y., Kabachnik M.I.
Solvent Extraction and Ion Exchange, 1986
23.
Safiulina A.M., Goryunov E.I., Letyushov A.A., Goryunova I.B., Smirnova S.A., Ginzburg A.G., Tananaev I.G., Nifant’ev E.E., Myasoedov B.F.
Mendeleev Communications, 2009
24.
β-Diphenylphosphorylated ketones: A general approach to the synthesis
Bodrin G.V., Goryunov E.I., Goryunova I.B., Nelyubina Y.V., Petrovskii P.V., Grigor’ev M.S., Safiulina A.M., Tananaev I.G., Nifant’ev E.E.
Doklady Chemistry, 2012
25.
Bradamante S., Pagani G.A.
Journal of Organic Chemistry, 1980
27.
Asymmetric addition of methyl nitroacetate to crotonaldehyde catalyzed by chiral amines
Belokon' Y.N., Kochetkov K.A., Churkina T.D., Ikonnikov N.S., Orlova S.A., Kuz'mina N.A., Bodrov D.E.
Russian Chemical Bulletin, 1993
28.
Asymmetric Michael reaction of diethyl malonate with crotonaldehyde catalyzed by chiral aminocarboxylates, amino alcoholates, and amino phenolates
Kochetkov K.A., Harutyunyan S.R., Kuz"mina N.A., Savel"eva T.F., Maleev V.I., Peregudov A.S., Vyskočil S., Sagiyan A.S.
Russian Chemical Bulletin, 2001
29.
Computer-aided prediction of QT-prolongation
Filz O., Lagunin A., Filimonov D., Poroikov V.
SAR and QSAR in Environmental Research, 2008
30.
The first enantioselective total syntheses of the allopumiliotoxin A alkaloids 267A and 339B
Goldstein S.W., Overman L.E., Rabinowitz M.H.
Journal of Organic Chemistry, 1992