Home / Publications / Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold

Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold

, 
Fedor Vladimirovich Ryzhkov 1
Fedor Vladimirovich Ryzhkov
, 
Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
, 
Tatiana Aleksandrovna Zaimovskaya 2
Tatiana Aleksandrovna Zaimovskaya
, 
Viktor Alfredovich Korolev 1
Viktor Alfredovich Korolev
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
10.1016/j.mencom.2016.09.011
Published 2016-09-08
Communication , Volume 26, Issue 5, 399-401
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Elinson M. N. et al. Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold // Mendeleev Communications. 2016. Vol. 26. No. 5. pp. 399-401.
GOST all authors (up to 50) Copy
Elinson M. N., Ryzhkov F. V., Vereshchagin A. N., Zaimovskaya T. A., Korolev V. A., Egorov M. P. Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold // Mendeleev Communications. 2016. Vol. 26. No. 5. pp. 399-401.
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TY - JOUR
DO - 10.1016/j.mencom.2016.09.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.09.011
TI - Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold
T2 - Mendeleev Communications
AU - Elinson, Michail Nikolaevich
AU - Ryzhkov, Fedor Vladimirovich
AU - Vereshchagin, Anatoly Nikolaevich
AU - Zaimovskaya, Tatiana Aleksandrovna
AU - Korolev, Viktor Alfredovich
AU - Egorov, Mikhail Petrovich
PY - 2016
DA - 2016/09/08
PB - Mendeleev Communications
SP - 399-401
IS - 5
VL - 26
ER -
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@article{2016_Elinson,
author = {Michail Nikolaevich Elinson and Fedor Vladimirovich Ryzhkov and Anatoly Nikolaevich Vereshchagin and Tatiana Aleksandrovna Zaimovskaya and Viktor Alfredovich Korolev and Mikhail Petrovich Egorov},
title = {Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold},
journal = {Mendeleev Communications},
year = {2016},
volume = {26},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.09.011},
number = {5},
pages = {399--401},
doi = {10.1016/j.mencom.2016.09.011}
}
MLA
Cite this
MLA Copy
Elinson, Michail Nikolaevich, et al. “Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4’-pyrano[3,2-c]pyridine]-2,5’(6’H)-dione scaffold.” Mendeleev Communications, vol. 26, no. 5, Sep. 2016, pp. 399-401. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.09.011.

Abstract

The new one-pot multicomponent assembling of isatins, malononitrile and 4 hydroxy-6-methylpyridin-2(1H)-ones into previously unknown 2’-amino-7’-methyl-2,5’-dioxo-5’,6’-dihydrospiro[indoline-3,4’-pyrano[3,2-c]pyridine]-3’-carbonitriles in 80–98% yields has been accomplished by their reflux in ethanol in the presence of sodium acetate.

References

1.
Pot economy and one-pot synthesis
Hayashi Y.
Chemical Science, 2016
3.
Ananikov V.P., Khokhlova E.A., Egorov M.P., Sakharov A.M., Zlotin S.G., Kucherov A.V., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications, 2015
4.
Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists
Evans B.E., Rittle K.E., Bock M.G., DiPardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S., Lotti V.J., Cerino D.J., Chen T.B., Kling P.J., Kunkel K.A., et. al.
Journal of Medicinal Chemistry, 1988
7.
A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of novel spiro-pyrrolothiazolyloxindoles and their antitubercular evaluation
Prasanna P., Balamurugan K., Perumal S., Yogeeswari P., Sriram D.
European Journal of Medicinal Chemistry, 2010
9.
Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity
Bhaskar G., Arun Y., Balachandran C., Saikumar C., Perumal P.T.
European Journal of Medicinal Chemistry, 2012
13.
Ethnobotany, phytochemistry and pharmacology of (Rubiaceae)
Heitzman Mary E, Neto Catherine C, Winiarz Elizabeth, Vaisberg Abraham J, Hammond Gerald B
Phytochemistry, 2005
14.
Chemical and Bioactive Constituents from Zanthoxylum simulans
Chen I., Wu S., Tsai I., Wu T., Pezzuto J.M., Lu M.C., Chai H., Suh N., Teng C.
Journal of Natural Products, 1994
15.
Structural Simplification of Bioactive Natural Products with Multicomponent Synthesis. 2. Antiproliferative and Antitubulin Activities of Pyrano[3,2-c]pyridones and Pyrano[3,2-c]quinolones
Magedov I.V., Manpadi M., Ogasawara M.A., Dhawan A.S., Rogelj S., Van slambrouck S., Steelant W.F., Evdokimov N.M., Uglinskii P.Y., Elias E.M., Knee E.J., Tongwa P., Antipin M.Y., Kornienko A.
Journal of Medicinal Chemistry, 2008
19.
Elinson M.N., Ilovaisky A.I., Merkulova V.M., Zaimovskaya T.A., Nikishin G.I.
Mendeleev Communications, 2012
23.
Demchuk D.V., Elinson M.N., Nikishin G.I.
Mendeleev Communications, 2011
24.
One-Pot ‘On-solvent’ Multicomponent Protocol for the Synthesis of Medicinally Relevant 4H-Pyrano[3,2-c]quinoline Scaffold
Vereshchagin A.N., Elinson M.N., Nasybullin R.F., Ryzhkov F.V., Bobrovsky S.I., Bushmarinov I.S., Egorov M.P.
Helvetica Chimica Acta, 2015
25.
“On Water”: Unique Reactivity of Organic Compounds in Aqueous Suspension
Narayan S., Muldoon J., Finn M.G., Fokin V.V., Kolb H.C., Sharpless K.B.
Angewandte Chemie - International Edition, 2005
28.
10.1016/j.mencom.2016.09.011_bib0140
Rosen
1991
31.
General approach to a spiro indole-3,1′-naphthalene tetracyclic system: stereoselective pseudo four-component reaction of isatins and cyclic ketones with two molecules of malononitrile
Elinson M.N., Vereshchagin A.N., Nasybullin R.F., Bobrovsky S.I., Ilovaisky A.I., Merkulova V.M., Bushmarinov I.S., Egorov M.P.
RSC Advances, 2015