Synthesis of Adamantylated Pyrimidines Using the Biginelli Reaction

Using an adamantane 3-oxonitrile and adamantane 1,3-dicarbonyl compounds in the three-component Biginelli reaction promoted by trimethylsilyl chloride, adamantylated pyrimidines are prepared. The reaction with the oxonitrile leads to 6-(1-adamantyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitri...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 48; no. 22; pp. 3965 - 3970
Main Authors Lashmanova, Eugeniya A., Rybakov, Victor B., Shiryaev, Andrey K.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.11.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
adamantane
SERIES
SOLVENT-FREE
3-oxonitriles
11-BETA-HSD1 INHIBITORS
RECENT PROGRESS
Biginelli reaction
1,3-dicarbonyl compounds
trimethylsilyl chloride
2-thioxo-1,2,3,4-tetrahydropyrimidines
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Summary:Using an adamantane 3-oxonitrile and adamantane 1,3-dicarbonyl compounds in the three-component Biginelli reaction promoted by trimethylsilyl chloride, adamantylated pyrimidines are prepared. The reaction with the oxonitrile leads to 6-(1-adamantyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles and/or 2-benzylidene-3-oxonitriles depending on the type of aromatic aldehyde. 1,3-Dicarbonyl adamantane compounds give 1-adamantyl(2-thioxo-1,2,3,4-tetrahydropyrimidine-5-yl) methanones with low yields. An adamantylated 2-thioxo-1,2,3,4-tetrahydropyrimidine is used to prepare thiazolo[3,2-alpha] pyrimidine derivatives.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1562459