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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.


Ruthenium–porphyrin complex-catalyzed three-component synthesis of aziridinylphosphonates and its proposed mechanism.
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C39: Ruthenium–porphyrin complex-catalyzed three-component synthesis of aziridinylphosphonates and its proposed mechanism.

Mentions: A ruthenium–porphyrin complex-catalyzed three-component reaction of α-diazophosphonates 180, nitrosoarenes 181, and alkynes 182 to give multifunctionalized aziridinylphosphonates 183 has been reported by Reddy et al. (Scheme 39) [77]. The desired aziridinylphosphonates 183 were isolated in 45–98% yields and 90:10 to >99:1 diastereoisomeric ratio depending on the structure of substituents present on nitrosoarenes 181 and alkynes 182. The use of internal alkynes gave only poor yields of the corresponding aziridinylphosphonates due to their low reactivity. This process involves the 1,3-dipolar cycloaddition of alkynes 182 with in situ generated nitrone 185 to afford isoxazolines 186 which rapidly rearrange to aziridinylphosphonates 183.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
Ruthenium–porphyrin complex-catalyzed three-component synthesis of aziridinylphosphonates and its proposed mechanism.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C39: Ruthenium–porphyrin complex-catalyzed three-component synthesis of aziridinylphosphonates and its proposed mechanism.
Mentions: A ruthenium–porphyrin complex-catalyzed three-component reaction of α-diazophosphonates 180, nitrosoarenes 181, and alkynes 182 to give multifunctionalized aziridinylphosphonates 183 has been reported by Reddy et al. (Scheme 39) [77]. The desired aziridinylphosphonates 183 were isolated in 45–98% yields and 90:10 to >99:1 diastereoisomeric ratio depending on the structure of substituents present on nitrosoarenes 181 and alkynes 182. The use of internal alkynes gave only poor yields of the corresponding aziridinylphosphonates due to their low reactivity. This process involves the 1,3-dipolar cycloaddition of alkynes 182 with in situ generated nitrone 185 to afford isoxazolines 186 which rapidly rearrange to aziridinylphosphonates 183.

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.