A multicomponent reaction towards N-(cyanomethyl)amides

N. Elders; E. Ruijter; F.J.J. de Kanter; E Janssen; M. Lutz; A.L Spek; R.V.A. Orru

doi:10.1002/chem.200900785

A multicomponent reaction towards N-(cyanomethyl)amides

N. Elders, E. Ruijter, F.J.J. de Kanter, E Janssen, M. Lutz, A.L Spek, R.V.A. Orru

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

Abstract

A study was conducted to demonstrate multicomponent reactions (MCR) towards N-(cyanomethyl)amides. A fourth MCR was developed from α-isocyano amides, amines, and carbonyl components. It was demonstrated that the resulting N-(cyanomethyl)amides were to be isolated in moderate to excellent yield using a wide range of primary and secondary amines, along with aldehydes and ketones. A number of functional groups were tolerated in addition to the broad substrate scope of the reaction, eliminating the need for protective groups and allowing direct post-modification. The results of the reaction were also directed toward 2H-2-imidazolines by modifying reaction conditions. The α-isocyano amides, aldehydes or ketones, and amines were stirred in MeOH in the presence of MgSO

Original language	English
Pages (from-to)	6096-6099
Number of pages	4
Journal	Chemistry: A European Journal
Volume	15
Issue number	25
Early online date	5 Jun 2009
DOIs	https://doi.org/10.1002/chem.200900785
Publication status	Published - 15 Jun 2009

Keywords

Amides/chemical synthesis
Catalysis
Imidazolines/chemistry
Molecular Structure
Nitriles/chemical synthesis
Silver/chemistry

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10.1002/chem.200900785

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CCDC 735704: Experimental Crystal Structure Determination
Elders, N. (Contributor), Ruijter, E. (Contributor), De Kanter, F. J. J. (Contributor), Janssen, E. (Contributor), Lutz, M. (Contributor), Spek, A. L. (Contributor) & Orru, R. V. A. (Contributor), Unknown Publisher, 15 Jun 2009
DOI: 10.5517/ccspkdd, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccspkdd&sid=DataCite
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title = "A multicomponent reaction towards N-(cyanomethyl)amides",

abstract = "A study was conducted to demonstrate multicomponent reactions (MCR) towards N-(cyanomethyl)amides. A fourth MCR was developed from α-isocyano amides, amines, and carbonyl components. It was demonstrated that the resulting N-(cyanomethyl)amides were to be isolated in moderate to excellent yield using a wide range of primary and secondary amines, along with aldehydes and ketones. A number of functional groups were tolerated in addition to the broad substrate scope of the reaction, eliminating the need for protective groups and allowing direct post-modification. The results of the reaction were also directed toward 2H-2-imidazolines by modifying reaction conditions. The α-isocyano amides, aldehydes or ketones, and amines were stirred in MeOH in the presence of MgSO",

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author = "N. Elders and E. Ruijter and {de Kanter}, F.J.J. and E Janssen and M. Lutz and A.L Spek and R.V.A. Orru",

year = "2009",

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doi = "10.1002/chem.200900785",

language = "English",

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AU - Elders, N.

AU - Ruijter, E.

AU - de Kanter, F.J.J.

AU - Janssen, E

AU - Lutz, M.

AU - Spek, A.L

AU - Orru, R.V.A.

PY - 2009/6/15

Y1 - 2009/6/15

N2 - A study was conducted to demonstrate multicomponent reactions (MCR) towards N-(cyanomethyl)amides. A fourth MCR was developed from α-isocyano amides, amines, and carbonyl components. It was demonstrated that the resulting N-(cyanomethyl)amides were to be isolated in moderate to excellent yield using a wide range of primary and secondary amines, along with aldehydes and ketones. A number of functional groups were tolerated in addition to the broad substrate scope of the reaction, eliminating the need for protective groups and allowing direct post-modification. The results of the reaction were also directed toward 2H-2-imidazolines by modifying reaction conditions. The α-isocyano amides, aldehydes or ketones, and amines were stirred in MeOH in the presence of MgSO

AB - A study was conducted to demonstrate multicomponent reactions (MCR) towards N-(cyanomethyl)amides. A fourth MCR was developed from α-isocyano amides, amines, and carbonyl components. It was demonstrated that the resulting N-(cyanomethyl)amides were to be isolated in moderate to excellent yield using a wide range of primary and secondary amines, along with aldehydes and ketones. A number of functional groups were tolerated in addition to the broad substrate scope of the reaction, eliminating the need for protective groups and allowing direct post-modification. The results of the reaction were also directed toward 2H-2-imidazolines by modifying reaction conditions. The α-isocyano amides, aldehydes or ketones, and amines were stirred in MeOH in the presence of MgSO

KW - Amides/chemical synthesis

KW - Catalysis

KW - Imidazolines/chemistry

KW - Molecular Structure

KW - Nitriles/chemical synthesis

KW - Silver/chemistry

U2 - 10.1002/chem.200900785

DO - 10.1002/chem.200900785

M3 - Article

C2 - 19462390

SN - 0947-6539

VL - 15

SP - 6096

EP - 6099

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

IS - 25

ER -

A multicomponent reaction towards N-(cyanomethyl)amides

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CCDC 735704: Experimental Crystal Structure Determination

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