Microwave-assisted silylation-amination of uracil acyclonucleosides to 4-alkylamino-2(1H)-Pyrimidinone analogues

Vincent Roy; Adam Mieczkowski; Dimitri Topalis; Sabine Berteina-Raboin; Dominique Deville-Bonne; Steven Patrick Nolan; Luigi A. Agrofoglio

doi:10.1055/s-2008-1067094

Microwave-assisted silylation-amination of uracil acyclonucleosides to 4-alkylamino-2(1H)-Pyrimidinone analogues

Vincent Roy, Adam Mieczkowski, Dimitri Topalis, Sabine Berteina-Raboin, Dominique Deville-Bonne, Steven Patrick Nolan, Luigi A. Agrofoglio

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Abstract

The synthesis of acyclic N-4-substituted cytosine nucleoside phosphonates using a microwave-assisted N-4-silylation-amination and olefin cross-metathesis as key assembly steps is described. The microwave-assisted silylation-arnination is compared to a conventional heating protocol. While yields and purities of the coupling products were comparable under both conditions, microwave heating allows a significant acceleration of the reaction (from 48 h to 5 h).

Original language	English
Pages (from-to)	2127-2133
Number of pages	7
Journal	Synthesis
Issue number	13
DOIs	https://doi.org/10.1055/s-2008-1067094
Publication status	Published - 1 Jul 2008

Keywords

microwaves
silylation-amination
olefin cross-metathesis
acyclic nucleoside phosphonates
NUCLEOSIDE PHOSPHONATE ANALOGS
CROSS-METATHESIS
PYRIMIDINE NUCLEOSIDES
CHEMISTRY
HETEROCYCLES
INFECTIONS
NUCLEOTIDE
THIATION

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title = "Microwave-assisted silylation-amination of uracil acyclonucleosides to 4-alkylamino-2(1H)-Pyrimidinone analogues",

abstract = "The synthesis of acyclic N-4-substituted cytosine nucleoside phosphonates using a microwave-assisted N-4-silylation-amination and olefin cross-metathesis as key assembly steps is described. The microwave-assisted silylation-arnination is compared to a conventional heating protocol. While yields and purities of the coupling products were comparable under both conditions, microwave heating allows a significant acceleration of the reaction (from 48 h to 5 h).",

keywords = "microwaves, silylation-amination, olefin cross-metathesis, acyclic nucleoside phosphonates, NUCLEOSIDE PHOSPHONATE ANALOGS, CROSS-METATHESIS, PYRIMIDINE NUCLEOSIDES, CHEMISTRY, HETEROCYCLES, INFECTIONS, NUCLEOTIDE, THIATION",

author = "Vincent Roy and Adam Mieczkowski and Dimitri Topalis and Sabine Berteina-Raboin and Dominique Deville-Bonne and Nolan, \{Steven Patrick\} and Agrofoglio, \{Luigi A.\}",

year = "2008",

month = jul,

day = "1",

doi = "10.1055/s-2008-1067094",

language = "English",

pages = "2127--2133",

journal = "Synthesis",

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publisher = "Georg Thieme Verlag",

number = "13",

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TY - JOUR

T1 - Microwave-assisted silylation-amination of uracil acyclonucleosides to 4-alkylamino-2(1H)-Pyrimidinone analogues

AU - Roy, Vincent

AU - Mieczkowski, Adam

AU - Topalis, Dimitri

AU - Berteina-Raboin, Sabine

AU - Deville-Bonne, Dominique

AU - Nolan, Steven Patrick

AU - Agrofoglio, Luigi A.

PY - 2008/7/1

Y1 - 2008/7/1

N2 - The synthesis of acyclic N-4-substituted cytosine nucleoside phosphonates using a microwave-assisted N-4-silylation-amination and olefin cross-metathesis as key assembly steps is described. The microwave-assisted silylation-arnination is compared to a conventional heating protocol. While yields and purities of the coupling products were comparable under both conditions, microwave heating allows a significant acceleration of the reaction (from 48 h to 5 h).

AB - The synthesis of acyclic N-4-substituted cytosine nucleoside phosphonates using a microwave-assisted N-4-silylation-amination and olefin cross-metathesis as key assembly steps is described. The microwave-assisted silylation-arnination is compared to a conventional heating protocol. While yields and purities of the coupling products were comparable under both conditions, microwave heating allows a significant acceleration of the reaction (from 48 h to 5 h).

KW - microwaves

KW - silylation-amination

KW - olefin cross-metathesis

KW - acyclic nucleoside phosphonates

KW - NUCLEOSIDE PHOSPHONATE ANALOGS

KW - CROSS-METATHESIS

KW - PYRIMIDINE NUCLEOSIDES

KW - CHEMISTRY

KW - HETEROCYCLES

KW - INFECTIONS

KW - NUCLEOTIDE

KW - THIATION

UR - https://www.scopus.com/pages/publications/47349122417

U2 - 10.1055/s-2008-1067094

DO - 10.1055/s-2008-1067094

M3 - Article

SN - 0039-7881

SP - 2127

EP - 2133

JO - Synthesis

JF - Synthesis

IS - 13

ER -

Microwave-assisted silylation-amination of uracil acyclonucleosides to 4-alkylamino-2(1H)-Pyrimidinone analogues

Abstract

Keywords

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