Home / Publications / Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates

Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates

Farough Nasiri 1
Farough Nasiri
, 
Kourosh Pourdavaie 1
Kourosh Pourdavaie
, 
Samiyeh Yosefdad 1
Samiyeh Yosefdad
, 
Bahareh Atashkar 1
Bahareh Atashkar
10.1016/j.mencom.2007.11.019
Published 2007-11-09
Communication , Volume 17, Issue 6, 352-353
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Nasiri F. et al. Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates // Mendeleev Communications. 2007. Vol. 17. No. 6. pp. 352-353.
GOST all authors (up to 50) Copy
Nasiri F., Pourdavaie K., Yosefdad S., Atashkar B. Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates // Mendeleev Communications. 2007. Vol. 17. No. 6. pp. 352-353.
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TY - JOUR
DO - 10.1016/j.mencom.2007.11.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.11.019
TI - Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates
T2 - Mendeleev Communications
AU - Nasiri, Farough
AU - Pourdavaie, Kourosh
AU - Yosefdad, Samiyeh
AU - Atashkar, Bahareh
PY - 2007
DA - 2007/11/09
PB - Mendeleev Communications
SP - 352-353
IS - 6
VL - 17
ER -
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@article{2007_Nasiri,
author = {Farough Nasiri and Kourosh Pourdavaie and Samiyeh Yosefdad and Bahareh Atashkar},
title = {Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates},
journal = {Mendeleev Communications},
year = {2007},
volume = {17},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.11.019},
number = {6},
pages = {352--353},
doi = {10.1016/j.mencom.2007.11.019}
}
MLA
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Nasiri, Farough, et al. “Reaction between dialkyl acetylenedicarboxylates and six-membered 1,3-diketones in the presence of trialkylamines: a convenient synthesis of alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates.” Mendeleev Communications, vol. 17, no. 6, Nov. 2007, pp. 352-353. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.11.019.

Keywords

Chromenes; acetylenic esters; trimethylamine; cyclic 1,3-diketones

Abstract

The reaction of dialkyl acetylenedicarboxylates with six-membered cyclic 1,3-diketones such as 1,3-cyclohexanedione or 5,5-dimethyl-1,3-cyclohexanedione in the presence of a catalytic amount of trimethylamine, triethylamine or tributylamine in CH2Cl2 leads to alkyl 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-4-carboxylates in good yields.

References

1.
R. O. Kennedy and R. D. Thornes, Coumarins: Biology, Applications and Mode of Action, John Wiley and Sons, Chichester, 1997.
2.
M. Maeda, Laser Dyes, Academic Press, New York, 1984.
3.
10.1016/j.mencom.2007.11.019_bib3_1
Mitra
J. Indian Chem. Soc., 1998
4.
An asymmetric approach to coumarin anticoagulants via hetero-Diels–Alder cycloaddition
Cravotto G., Nano G.M., Palmisano G., Tagliapietra S.
Tetrahedron Asymmetry, 2001
7.
A novel class of inhibitors for steroid 5α-Reductase: synthesis and evaluation of umbelliferone derivatives
Fan G., Mar W., Park M.K., Wook Choi E., Kim K., Kim S.
Bioorganic and Medicinal Chemistry Letters, 2001
8.
Structure–activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors
Kirkiacharian S., Thuy D.T., Sicsic S., Bakhchinian R., Kurkjian R., Tonnaire T.
Il Farmaco, 2002
9.
10.1016/j.mencom.2007.11.019_bib8_1
Staunton
Oxford, 1979
10.
Biosynthesis of Coumarins
Matern U., Lüer P., Kreusch D.
1999
12.
J. D. Hepworth, in Comprehensive Heterocyclic Chemistry, eds. A. J. Boulton and A. McKillop, Pergamon, Oxford, 1984, vol. 3, pp. 799–810.
14.
The Thermal α-Substitution of Dimedone by Vinyl Ethers
Pinhey J., Xuan P.
Australian Journal of Chemistry, 1988
15.
Triphenylphosphine Catalized Reaction Between 1,3-Dicarbonyl Compounds and Acetylenic Esters
Yavari I., Nasiri F., Djahaniani H.
Phosphorus, Sulfur and Silicon and the Related Elements, 2003
16.
10.1016/j.mencom.2007.11.019_bib11_1
Yavari
Pol. J. Chem., 2004
20.
Strategies for Heterocyclic Construction via Novel Multicomponent Reactions Based on Isocyanides and Nucleophilic Carbenes
Nair V., Rajesh C., Vinod A.U., Bindu S., Sreekanth A.R., Mathen J.S., Balagopal L.
Accounts of Chemical Research, 2003