4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil

Madjid Ait Sidhoum; Laurent El Kaïm; Laurence Grimaud

doi:10.1016/j.tet.2018.04.058

4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil

Madjid Ait Sidhoum
, Laurent El Kaïm
, Laurence Grimaud

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

Abstract

The Ugi-Smiles reaction of S-benzyl thiouracil have been exploited in several three-step sequences for the preparation of aminopyrimidine libraries with high diversity. After the 4-component coupling, oxidation of the thioether to sulfone is followed by displacement of the latter by various carbon-centered nucleophiles (cyanide, malonate, boronic acids) or amines. The efficiency of the whole sequence was further demonstrated with one-pot procedures.

Original language	English
Pages (from-to)	5222-5231
Number of pages	10
Journal	Tetrahedron
Volume	74
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2018.04.058
Publication status	Published - 20 Sept 2018
Externally published	Yes

Keywords

Pyrimidines
Sulfone
Suzuki reaction
Ugi-smiles

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10.1016/j.tet.2018.04.058

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title = "4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil",

abstract = "The Ugi-Smiles reaction of S-benzyl thiouracil have been exploited in several three-step sequences for the preparation of aminopyrimidine libraries with high diversity. After the 4-component coupling, oxidation of the thioether to sulfone is followed by displacement of the latter by various carbon-centered nucleophiles (cyanide, malonate, boronic acids) or amines. The efficiency of the whole sequence was further demonstrated with one-pot procedures.",

keywords = "Pyrimidines, Sulfone, Suzuki reaction, Ugi-smiles",

author = "Sidhoum, \{Madjid Ait\} and \{El Ka{\"i}m\}, Laurent and Laurence Grimaud",

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doi = "10.1016/j.tet.2018.04.058",

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AU - Sidhoum, Madjid Ait

AU - El Kaïm, Laurent

AU - Grimaud, Laurence

PY - 2018/9/20

Y1 - 2018/9/20

N2 - The Ugi-Smiles reaction of S-benzyl thiouracil have been exploited in several three-step sequences for the preparation of aminopyrimidine libraries with high diversity. After the 4-component coupling, oxidation of the thioether to sulfone is followed by displacement of the latter by various carbon-centered nucleophiles (cyanide, malonate, boronic acids) or amines. The efficiency of the whole sequence was further demonstrated with one-pot procedures.

AB - The Ugi-Smiles reaction of S-benzyl thiouracil have been exploited in several three-step sequences for the preparation of aminopyrimidine libraries with high diversity. After the 4-component coupling, oxidation of the thioether to sulfone is followed by displacement of the latter by various carbon-centered nucleophiles (cyanide, malonate, boronic acids) or amines. The efficiency of the whole sequence was further demonstrated with one-pot procedures.

KW - Pyrimidines

KW - Sulfone

KW - Suzuki reaction

KW - Ugi-smiles

U2 - 10.1016/j.tet.2018.04.058

DO - 10.1016/j.tet.2018.04.058

M3 - Article

AN - SCOPUS:85046157652

SN - 0040-4020

VL - 74

SP - 5222

EP - 5231

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

4-Aminopyrimidine libraries from the Ugi-Smiles reaction of thiouracil

Abstract

Keywords

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