Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system

Michail N. Elinson; Alexey I. Ilovaisky; Alexander S. Dorofeev; Valentina M. Merkulova; Nikita O. Stepanov; Fedor M. Miloserdov; Yuri N. Ogibin; Gennady I. Nikishin

doi:10.1016/j.tet.2007.07.080

Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system

Michail N. Elinson^*, Alexey I. Ilovaisky, Alexander S. Dorofeev, Valentina M. Merkulova, Nikita O. Stepanov, Fedor M. Miloserdov, Yuri N. Ogibin, Gennady I. Nikishin

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

97 Citations (Scopus)

Abstract

An electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized 5,6,7,8-tetrahydro-4H-chromene system in 83-98% yields. The application of this efficient electrocatalytic method to the formation of medicinally relevant spirocyclic (4H-chromene)-4,3′-oxindoles is beneficial from the viewpoint of diversity-oriented large-scale processes and represents novel, facile, and environmentally benign synthetic concept for multicomponent reaction strategy.

Original language	English
Pages (from-to)	10543-10548
Number of pages	6
Journal	Tetrahedron
Volume	63
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2007.07.080
Publication status	Published - 15 Jan 2007
Externally published	Yes

Keywords

Chromenes
Electrocatalysis
Electrochemistry
Multicomponent reactions
Spirooxindoles

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10.1016/j.tet.2007.07.080

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Elinson, M. N., Ilovaisky, A. I., Dorofeev, A. S., Merkulova, V. M., Stepanov, N. O., Miloserdov, F. M., Ogibin, Y. N., & Nikishin, G. I. (2007). Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system. Tetrahedron, 63(42), 10543-10548. https://doi.org/10.1016/j.tet.2007.07.080

@article{e79975994410402bacb3b21c81c57bc9,

title = "Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system",

abstract = "An electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized 5,6,7,8-tetrahydro-4H-chromene system in 83-98% yields. The application of this efficient electrocatalytic method to the formation of medicinally relevant spirocyclic (4H-chromene)-4,3′-oxindoles is beneficial from the viewpoint of diversity-oriented large-scale processes and represents novel, facile, and environmentally benign synthetic concept for multicomponent reaction strategy.",

keywords = "Chromenes, Electrocatalysis, Electrochemistry, Multicomponent reactions, Spirooxindoles",

author = "Elinson, {Michail N.} and Ilovaisky, {Alexey I.} and Dorofeev, {Alexander S.} and Merkulova, {Valentina M.} and Stepanov, {Nikita O.} and Miloserdov, {Fedor M.} and Ogibin, {Yuri N.} and Nikishin, {Gennady I.}",

year = "2007",

month = jan,

day = "15",

doi = "10.1016/j.tet.2007.07.080",

language = "English",

volume = "63",

pages = "10543--10548",

journal = "Tetrahedron",

issn = "0040-4020",

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Elinson, MN, Ilovaisky, AI, Dorofeev, AS, Merkulova, VM, Stepanov, NO, Miloserdov, FM, Ogibin, YN & Nikishin, GI 2007, 'Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system', Tetrahedron, vol. 63, no. 42, pp. 10543-10548. https://doi.org/10.1016/j.tet.2007.07.080

Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system. / Elinson, Michail N.; Ilovaisky, Alexey I.; Dorofeev, Alexander S. et al.
In: Tetrahedron, Vol. 63, No. 42, 15.01.2007, p. 10543-10548.

Research output: Contribution to journal › Article › Academic › peer-review

TY - JOUR

T1 - Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile

T2 - facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system

AU - Elinson, Michail N.

AU - Ilovaisky, Alexey I.

AU - Dorofeev, Alexander S.

AU - Merkulova, Valentina M.

AU - Stepanov, Nikita O.

AU - Miloserdov, Fedor M.

AU - Ogibin, Yuri N.

AU - Nikishin, Gennady I.

PY - 2007/1/15

Y1 - 2007/1/15

N2 - An electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized 5,6,7,8-tetrahydro-4H-chromene system in 83-98% yields. The application of this efficient electrocatalytic method to the formation of medicinally relevant spirocyclic (4H-chromene)-4,3′-oxindoles is beneficial from the viewpoint of diversity-oriented large-scale processes and represents novel, facile, and environmentally benign synthetic concept for multicomponent reaction strategy.

AB - An electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile in alcohols in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized 5,6,7,8-tetrahydro-4H-chromene system in 83-98% yields. The application of this efficient electrocatalytic method to the formation of medicinally relevant spirocyclic (4H-chromene)-4,3′-oxindoles is beneficial from the viewpoint of diversity-oriented large-scale processes and represents novel, facile, and environmentally benign synthetic concept for multicomponent reaction strategy.

KW - Chromenes

KW - Electrocatalysis

KW - Electrochemistry

KW - Multicomponent reactions

KW - Spirooxindoles

U2 - 10.1016/j.tet.2007.07.080

DO - 10.1016/j.tet.2007.07.080

M3 - Article

AN - SCOPUS:34548314643

SN - 0040-4020

VL - 63

SP - 10543

EP - 10548

JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

Elinson MN, Ilovaisky AI, Dorofeev AS, Merkulova VM, Stepanov NO, Miloserdov FM et al. Electrocatalytic multicomponent transformation of cyclic 1,3-diketones, isatins, and malononitrile: facile and convenient way to functionalized spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3′-oxindole system. Tetrahedron. 2007 Jan 15;63(42):10543-10548. doi: 10.1016/j.tet.2007.07.080