Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion

Jurriën W. Collet; Bénédicte Morel; Hung Chien Lin; Thomas R. Roose; Pieter Mampuys; Romano V.A. Orru; Eelco Ruijter; Bert U.W. Maes

doi:10.1021/acs.orglett.9b04387

Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion

Jurriën W. Collet
, Bénédicte Morel
, Hung Chien Lin
, Thomas R. Roose
, Pieter Mampuys
, Romano V.A. Orru^*
, Eelco Ruijter
, Bert U.W. Maes

^*Corresponding author for this work

AIMMS

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

Abstract

A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available N-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., green solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and N-uracil-amidines that are tolerated make this method an interesting alternative to the currently available procedures toward pyrimidouracils.

Original language	English
Pages (from-to)	914-919
Number of pages	6
Journal	Organic letters
Volume	22
Issue number	3
Early online date	16 Jan 2020
DOIs	https://doi.org/10.1021/acs.orglett.9b04387
Publication status	Published - 7 Feb 2020

Funding

Financial support from The Netherlands Organization for Scientific Research (NWO), the Research Foundation Flanders (FWO), the Francqui Foundation, and the University of Antwerp (BOF Scholarship to J.W.C.) is gratefully acknowledged. The research leading to these results has also received support from the Innovative Medicines Initiative ( www.imi.europa.eu ) Joint Undertaking under Grant Agreement No. 115360, resources of which are composed of financial contribution from the European Union’s Seventh Framework Programme (FP7/2007-2013) and EFPIA companies’ in kind contribution.

Funders	Funder number
Bijzonder Onderzoeksfonds UGent
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Francqui Foundation
Fonds Wetenschappelijk Onderzoek
European Commission
Universiteit Antwerpen
Innovative Medicines Initiative
Seventh Framework Programme	115360

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 6 Clean Water and Sanitation

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title = "Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion",

abstract = "A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available N-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., green solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and N-uracil-amidines that are tolerated make this method an interesting alternative to the currently available procedures toward pyrimidouracils.",

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year = "2020",

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doi = "10.1021/acs.orglett.9b04387",

language = "English",

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T1 - Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion

AU - Collet, Jurriën W.

AU - Morel, Bénédicte

AU - Lin, Hung Chien

AU - Roose, Thomas R.

AU - Mampuys, Pieter

AU - Orru, Romano V.A.

AU - Ruijter, Eelco

AU - Maes, Bert U.W.

PY - 2020/2/7

Y1 - 2020/2/7

N2 - A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available N-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., green solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and N-uracil-amidines that are tolerated make this method an interesting alternative to the currently available procedures toward pyrimidouracils.

AB - A robust nickel-catalyzed oxidative isocyanide insertion/C-H amination by reaction of readily available N-uracil-amidines with isocyanides affording polysubstituted pyrimidouracils has been reported. The reaction proceeds in moderate to quantitative yield, under mild conditions (i.e., green solvent, air atmosphere, moderate temperature). The broad range of structurally diverse isocyanides and N-uracil-amidines that are tolerated make this method an interesting alternative to the currently available procedures toward pyrimidouracils.

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DO - 10.1021/acs.orglett.9b04387

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SP - 914

EP - 919

JO - Organic letters

JF - Organic letters

IS - 3

ER -

Synthesis of Densely Functionalized Pyrimidouracils by Nickel(II)-Catalyzed Isocyanide Insertion

Abstract

Funding

UN SDGs

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