Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

Monica Paravidino; Robin S. Bon; Rachel Scheffelaar; Danielle J. Vugts; Anass Znabet; Rob F. Schmitz; Frans J.J. De Kanter; Martin Lutz; Anthony L. Spek; Marinus B. Groen; Romano V.A. Orru

doi:https://doi.org/10.1021/ol062204b

Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

Monica Paravidino, Robin S. Bon, Rachel Scheffelaar, Danielle J. Vugts, Anass Znabet, Rob F. Schmitz, Frans J.J. De Kanter, Martin Lutz, Anthony L. Spek, Marinus B. Groen, Romano V.A. Orru

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

49 Citations (Scopus)

Abstract

In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation.

Original language	English
Pages (from-to)	5369-5372
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	23
DOIs	https://doi.org/10.1021/ol062204b
Publication status	Published - 9 Nov 2006
Externally published	Yes

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title = "Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality",

abstract = "In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation.",

author = "Monica Paravidino and Bon, {Robin S.} and Rachel Scheffelaar and Vugts, {Danielle J.} and Anass Znabet and Schmitz, {Rob F.} and {De Kanter}, {Frans J.J.} and Martin Lutz and Spek, {Anthony L.} and Groen, {Marinus B.} and Orru, {Romano V.A.}",

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doi = "https://doi.org/10.1021/ol062204b",

language = "English",

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TY - JOUR

T1 - Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

AU - Paravidino, Monica

AU - Bon, Robin S.

AU - Scheffelaar, Rachel

AU - Vugts, Danielle J.

AU - Znabet, Anass

AU - Schmitz, Rob F.

AU - De Kanter, Frans J.J.

AU - Lutz, Martin

AU - Spek, Anthony L.

AU - Groen, Marinus B.

AU - Orru, Romano V.A.

PY - 2006/11/9

Y1 - 2006/11/9

N2 - In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation.

AB - In a search for new multicomponent strategies leading to valuable small heterocycles, a new highly diastereoselective four-component reaction (4CR) was found in which a phosphonate, nitriles, aldehydes, and isocyanoacetates combine to afford functionalized 3-isocyano-3,4-dihydro-2-pyridones. In this strategy, initially a 1-azadiene is generated, which is trapped in the same pot by an isocyanoacetate as the fourth component. Multicomponent reactions (MCRs) that lead to heterocycles containing isocyano substituents are unprecedented and offer many possibilities for further differentiation.

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U2 - https://doi.org/10.1021/ol062204b

DO - https://doi.org/10.1021/ol062204b

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VL - 8

SP - 5369

EP - 5372

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Diastereoselective multicomponent synthesis of dihydropyridones with an isocyanide functionality

Abstract

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