Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings

Francesca Brunelli; Camilla Russo; Ubaldina Galli; Mariateresa Giustiniano; Gian Cesare Tron

doi:10.1016/j.tetlet.2021.153513

Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings

Francesca Brunelli, Camilla Russo, Ubaldina Galli, Mariateresa Giustiniano, Gian Cesare Tron

Department of Pharmaceutical Sciences

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

Abstract

An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-heterocyclic rings (imidazole, benzimidazole, triazole, benzotriazole and tetrazole) affords a hitherto unknown class of compounds which cannot be obtained via a classical multistep two-component reaction. From this work, it appears evident: a) kinetic control dictated by the [3 + 1] cycloaddition between nitrile N-oxides and isocyanides; b) the chemical compatibility between the highly unstable nitrilium ion and the poorly nucleophilic imidazoles and related heterocycles, which quench the reaction allowing for the formation of a single product.

Original language	English
Article number	153513
Journal	Tetrahedron Letters
Volume	86
DOIs	https://doi.org/10.1016/j.tetlet.2021.153513
Publication status	Published - 7 Dec 2021

Keywords

Isocyanide
Multicomponent reaction
Nitrile-N-oxide
Nitrilium ion

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10.1016/j.tetlet.2021.153513

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title = "Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings",

abstract = "An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-heterocyclic rings (imidazole, benzimidazole, triazole, benzotriazole and tetrazole) affords a hitherto unknown class of compounds which cannot be obtained via a classical multistep two-component reaction. From this work, it appears evident: a) kinetic control dictated by the [3 + 1] cycloaddition between nitrile N-oxides and isocyanides; b) the chemical compatibility between the highly unstable nitrilium ion and the poorly nucleophilic imidazoles and related heterocycles, which quench the reaction allowing for the formation of a single product.",

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T1 - Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings

AU - Brunelli, Francesca

AU - Russo, Camilla

AU - Galli, Ubaldina

AU - Giustiniano, Mariateresa

AU - Tron, Gian Cesare

PY - 2021/12/7

Y1 - 2021/12/7

N2 - An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-heterocyclic rings (imidazole, benzimidazole, triazole, benzotriazole and tetrazole) affords a hitherto unknown class of compounds which cannot be obtained via a classical multistep two-component reaction. From this work, it appears evident: a) kinetic control dictated by the [3 + 1] cycloaddition between nitrile N-oxides and isocyanides; b) the chemical compatibility between the highly unstable nitrilium ion and the poorly nucleophilic imidazoles and related heterocycles, which quench the reaction allowing for the formation of a single product.

AB - An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-heterocyclic rings (imidazole, benzimidazole, triazole, benzotriazole and tetrazole) affords a hitherto unknown class of compounds which cannot be obtained via a classical multistep two-component reaction. From this work, it appears evident: a) kinetic control dictated by the [3 + 1] cycloaddition between nitrile N-oxides and isocyanides; b) the chemical compatibility between the highly unstable nitrilium ion and the poorly nucleophilic imidazoles and related heterocycles, which quench the reaction allowing for the formation of a single product.

KW - Isocyanide

KW - Multicomponent reaction

KW - Nitrile-N-oxide

KW - Nitrilium ion

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U2 - 10.1016/j.tetlet.2021.153513

DO - 10.1016/j.tetlet.2021.153513

M3 - Article

SN - 0040-4039

VL - 86

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153513

ER -

Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings

Abstract

Keywords

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