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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.


Three-component reaction of acylphosphonates, isocyanides and dialkyl acetylenedicarboxylate to afford 2-phosphonofuran derivatives.
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C41: Three-component reaction of acylphosphonates, isocyanides and dialkyl acetylenedicarboxylate to afford 2-phosphonofuran derivatives.

Mentions: A one-pot three-component reaction between the acylphosphonates 192 formed by treatment of triethyl phosphite and acyl chlorides 191, isocyanides 193 and dialkyl acetylenedicarboxylates 194 to afford 2-phosphonofuran derivatives 196 has been reported by our group (Scheme 41) [79]. The desired furanylphosphonates were isolated in 52–67% yield at rt in CH2Cl2. In this transformation the zwitterionic intermediate 195, resulting from reaction of isocyanide with dialkyl acetylenedicarboxylate, added to the carbonyl group of the acylphosphonate followed by an intramolecular cyclization.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
Three-component reaction of acylphosphonates, isocyanides and dialkyl acetylenedicarboxylate to afford 2-phosphonofuran derivatives.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C41: Three-component reaction of acylphosphonates, isocyanides and dialkyl acetylenedicarboxylate to afford 2-phosphonofuran derivatives.
Mentions: A one-pot three-component reaction between the acylphosphonates 192 formed by treatment of triethyl phosphite and acyl chlorides 191, isocyanides 193 and dialkyl acetylenedicarboxylates 194 to afford 2-phosphonofuran derivatives 196 has been reported by our group (Scheme 41) [79]. The desired furanylphosphonates were isolated in 52–67% yield at rt in CH2Cl2. In this transformation the zwitterionic intermediate 195, resulting from reaction of isocyanide with dialkyl acetylenedicarboxylate, added to the carbonyl group of the acylphosphonate followed by an intramolecular cyclization.

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.