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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.


Trimethylchlorosilane-mediated Biginelli reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate.
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C3: Trimethylchlorosilane-mediated Biginelli reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate.

Mentions: The trimethylchlorosilane-mediated one-pot reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate (8) with aryl aldehydes 9 and urea under Biginelli conditions has been presented by Timoshenko et al. (Scheme 3) [27]. The resulting 4-hydroxytetrahydropyrimidin-2-ones 10 were unstable and underwent dephosphorylation to give dihydropyrimidin-2-ones 11 after one week at room temperature. Also, heating of either the reactants or product 10 in the presence of acetic acid led to the formation of dihydropyrimidin-2-ones 11 (Scheme 3).


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
Trimethylchlorosilane-mediated Biginelli reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C3: Trimethylchlorosilane-mediated Biginelli reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate.
Mentions: The trimethylchlorosilane-mediated one-pot reaction of diethyl (3,3,3-trifluoropropyl-2-oxo)phosphonate (8) with aryl aldehydes 9 and urea under Biginelli conditions has been presented by Timoshenko et al. (Scheme 3) [27]. The resulting 4-hydroxytetrahydropyrimidin-2-ones 10 were unstable and underwent dephosphorylation to give dihydropyrimidin-2-ones 11 after one week at room temperature. Also, heating of either the reactants or product 10 in the presence of acetic acid led to the formation of dihydropyrimidin-2-ones 11 (Scheme 3).

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.