Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3- carboxylates and 3-carbonitriles

Xingxian Gu; Gunda I. Georg

doi:10.1016/j.tet.2013.08.081

Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3- carboxylates and 3-carbonitriles

Xingxian Gu, Gunda I. Georg

Medicinal Chemistry

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8 Scopus citations

Abstract

Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.

Original language	English (US)
Pages (from-to)	9406-9416
Number of pages	11
Journal	Tetrahedron
Volume	69
Issue number	45
DOIs	https://doi.org/10.1016/j.tet.2013.08.081
State	Published - Nov 11 2013

Bibliographical note

Funding Information:
We gratefully acknowledge financial support from the NIH ( Grant No. P41 GM076302 and P41 GM081267 ) and the University of Minnesota through the Vince and McKnight Endowed Chairs (to G.I.G).

Keywords

2,5-Dioxooctahydroquinolines
Acetic anhydride
Catalysis
Lithium perchlorate
Multicomponent reaction
Triphenylphosphine

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title = "Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3- carboxylates and 3-carbonitriles",

abstract = "Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.",

keywords = "2,5-Dioxooctahydroquinolines, Acetic anhydride, Catalysis, Lithium perchlorate, Multicomponent reaction, Triphenylphosphine",

author = "Xingxian Gu and Georg, {Gunda I.}",

note = "Funding Information: We gratefully acknowledge financial support from the NIH ( Grant No. P41 GM076302 and P41 GM081267 ) and the University of Minnesota through the Vince and McKnight Endowed Chairs (to G.I.G). ",

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AU - Gu, Xingxian

AU - Georg, Gunda I.

N1 - Funding Information: We gratefully acknowledge financial support from the NIH ( Grant No. P41 GM076302 and P41 GM081267 ) and the University of Minnesota through the Vince and McKnight Endowed Chairs (to G.I.G).

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Y1 - 2013/11/11

N2 - Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.

AB - Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates. When methyl cyanoacetate was subjected to the same reaction conditions in the presence of a catalytic amount of triphenylphosphine, the bicyclic 2,5-dioxooctahydroquinoline-3- carbonitriles were obtained in a one-flask reaction.

KW - 2,5-Dioxooctahydroquinolines

KW - Acetic anhydride

KW - Catalysis

KW - Lithium perchlorate

KW - Multicomponent reaction

KW - Triphenylphosphine

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ER -

Lithium perchlorate-, acetic anhydride-, and triphenylphosphine-assisted multicomponent syntheses of 4-unsubstituted 2,5-dioxooctahydroquinoline-3- carboxylates and 3-carbonitriles

Abstract

Bibliographical note

Keywords

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