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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.


FeCl3 and PdCl2 co-catalyzed three-component reaction of 2-alkynylbenzaldehydes, anilines, and diethyl phosphonate.
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C18: FeCl3 and PdCl2 co-catalyzed three-component reaction of 2-alkynylbenzaldehydes, anilines, and diethyl phosphonate.

Mentions: An efficient method for the synthetic preparation of diverse (2H-isoindol-1-yl)phosphonates 74 is an FeCl3-catalyzed Kabachnik–Fields reaction of 2-alkynylbenzaldehydes 72, anilines 73, and phosphonates followed by a PdCl2-catalyzed 5-exo-dig cyclization (Scheme 18) [45]. The desired (2H-isoindol-1-yl)phosphonates 74 were obtained under optimized conditions (5 mol % of FeCl3, 5 mol % of PdCl2, DCE/CH3CN, 60 °C) in good to excellent yields. One limitation is the use of aromatic aldehydes bearing electron-donating substituents which afforded the desired products in only low yields, because of their reduced electrophilicity. Aliphatic amines were unreactive in this transformation and only arylamines were found to be effective in this reaction. Eventually, the biological evaluation of the (2H-isoindol-1-yl)phosphonates 74 revealed their potential as HCT-116 inhibitors.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
FeCl3 and PdCl2 co-catalyzed three-component reaction of 2-alkynylbenzaldehydes, anilines, and diethyl phosphonate.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C18: FeCl3 and PdCl2 co-catalyzed three-component reaction of 2-alkynylbenzaldehydes, anilines, and diethyl phosphonate.
Mentions: An efficient method for the synthetic preparation of diverse (2H-isoindol-1-yl)phosphonates 74 is an FeCl3-catalyzed Kabachnik–Fields reaction of 2-alkynylbenzaldehydes 72, anilines 73, and phosphonates followed by a PdCl2-catalyzed 5-exo-dig cyclization (Scheme 18) [45]. The desired (2H-isoindol-1-yl)phosphonates 74 were obtained under optimized conditions (5 mol % of FeCl3, 5 mol % of PdCl2, DCE/CH3CN, 60 °C) in good to excellent yields. One limitation is the use of aromatic aldehydes bearing electron-donating substituents which afforded the desired products in only low yields, because of their reduced electrophilicity. Aliphatic amines were unreactive in this transformation and only arylamines were found to be effective in this reaction. Eventually, the biological evaluation of the (2H-isoindol-1-yl)phosphonates 74 revealed their potential as HCT-116 inhibitors.

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.