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Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

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ABSTRACT

Multicomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

No MeSH data available.


p-Toluenesulfonic acid-promoted Biginelli reaction of β-ketophosphonates, aryl aldehydes and urea.
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C5: p-Toluenesulfonic acid-promoted Biginelli reaction of β-ketophosphonates, aryl aldehydes and urea.

Mentions: Idris Essid and Soufiane Touil showed that the Biginelli condensation of β-ketophosphonates was highly sensitive to the nature of solvents, acid catalysts and reactants [28]. They found that the use of inorganic acids including HCl and H2SO4 or Lewis acids such as SnCl2, FeCl3 and VCl3, as well as heterogeneous catalysts including silica gel supported sulfuric acid and sodium hydrogen sulfate did not affect this reaction. Also, the reaction in the presence of p-toluenesulfonic acid (TsOH), in aprotic solvents proceeded with much better yields than in protic solvents. When diethyl (2-oxopropyl)phosphonate and 4-nitrobenzaldehyde were treated in the presence of 50 mol % TsOH in acetonitrile, 5-phosphonato-3,4-dihydropyrimidin-2-one 18 was obtained in excellent yield (Scheme 5).


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
p-Toluenesulfonic acid-promoted Biginelli reaction of β-ketophosphonates, aryl aldehydes and urea.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979670&req=5

C5: p-Toluenesulfonic acid-promoted Biginelli reaction of β-ketophosphonates, aryl aldehydes and urea.
Mentions: Idris Essid and Soufiane Touil showed that the Biginelli condensation of β-ketophosphonates was highly sensitive to the nature of solvents, acid catalysts and reactants [28]. They found that the use of inorganic acids including HCl and H2SO4 or Lewis acids such as SnCl2, FeCl3 and VCl3, as well as heterogeneous catalysts including silica gel supported sulfuric acid and sodium hydrogen sulfate did not affect this reaction. Also, the reaction in the presence of p-toluenesulfonic acid (TsOH), in aprotic solvents proceeded with much better yields than in protic solvents. When diethyl (2-oxopropyl)phosphonate and 4-nitrobenzaldehyde were treated in the presence of 50 mol % TsOH in acetonitrile, 5-phosphonato-3,4-dihydropyrimidin-2-one 18 was obtained in excellent yield (Scheme 5).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

Multicomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given.

No MeSH data available.