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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.


A domino Knoevenagel/phospha-Michael process for the synthesis of 2-oxoindolin-3-ylphosphonates.
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C31: A domino Knoevenagel/phospha-Michael process for the synthesis of 2-oxoindolin-3-ylphosphonates.

Mentions: A convenient one-pot ZnO nanorods-catalyzed reaction of isatin derivatives 144 with malononitrile (145) and dialkyl or diphenyl phosphonates 146 has been performed to give 2-oxindolin-3-ylphosphonates 147 (Scheme 31) [56]. The products were obtained in good to excellent yields using 10 mol % of the catalyst under solvent-free conditions at room temperature. However, when using ethyl cyanomalonate instead of malononitrile, the reaction in water led to the corresponding 2-oxoindolin-3-ylphosphonate in good yield. Further, the investigations showed that the recovered ZnO nanorods could be reused up to five times.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
A domino Knoevenagel/phospha-Michael process for the synthesis of 2-oxoindolin-3-ylphosphonates.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C31: A domino Knoevenagel/phospha-Michael process for the synthesis of 2-oxoindolin-3-ylphosphonates.
Mentions: A convenient one-pot ZnO nanorods-catalyzed reaction of isatin derivatives 144 with malononitrile (145) and dialkyl or diphenyl phosphonates 146 has been performed to give 2-oxindolin-3-ylphosphonates 147 (Scheme 31) [56]. The products were obtained in good to excellent yields using 10 mol % of the catalyst under solvent-free conditions at room temperature. However, when using ethyl cyanomalonate instead of malononitrile, the reaction in water led to the corresponding 2-oxoindolin-3-ylphosphonate in good yield. Further, the investigations showed that the recovered ZnO nanorods could be reused up to five times.

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.