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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.


One-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate.
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C22: One-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate.

Mentions: 2.2.7 Isoquinolone-1-phosphonates: From Lewis acid catalyzed 6-endo-dig cyclizations of acetylenic Kabachnik–Fields adducts: A modified Kabachnik–Fields reaction for the synthesis of isoquinoline-1-phosphonate derivatives is the three-component reaction of acetylenic aldehydes with various amines and dialkyl phosphonates followed by Lewis acid catalyzed 6-endo-dig cyclizations. Wu et al. reported the one-pot reaction of 2-alkynylbenzaldehydes 96, amines 97, and diethyl phosphonate to afford (2,3-disubstituted-1,2-dihydroisoquinolin-1-yl)phosphonates 98 in the presence of various Lewis acids (Scheme 22) [47–48]. This reaction, under catalyst-free conditions or in the presence of Lewis acids such as FeCl3, CBr4, In(OTf)3, Bi(OTf)3, and Yb(OTf)3, exclusively yielded the acyclic α-aminophosphonates 99. However, the reaction in the presence of AgOTf (5 mol %) or CuI (10 mol %) at 60 °C led to isoquinolin-1-ylphosphonates 98 in moderate to high yields.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
One-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C22: One-pot three-component reaction of 2-alkynylbenzaldehydes, amines, and diethyl phosphonate.
Mentions: 2.2.7 Isoquinolone-1-phosphonates: From Lewis acid catalyzed 6-endo-dig cyclizations of acetylenic Kabachnik–Fields adducts: A modified Kabachnik–Fields reaction for the synthesis of isoquinoline-1-phosphonate derivatives is the three-component reaction of acetylenic aldehydes with various amines and dialkyl phosphonates followed by Lewis acid catalyzed 6-endo-dig cyclizations. Wu et al. reported the one-pot reaction of 2-alkynylbenzaldehydes 96, amines 97, and diethyl phosphonate to afford (2,3-disubstituted-1,2-dihydroisoquinolin-1-yl)phosphonates 98 in the presence of various Lewis acids (Scheme 22) [47–48]. This reaction, under catalyst-free conditions or in the presence of Lewis acids such as FeCl3, CBr4, In(OTf)3, Bi(OTf)3, and Yb(OTf)3, exclusively yielded the acyclic α-aminophosphonates 99. However, the reaction in the presence of AgOTf (5 mol %) or CuI (10 mol %) at 60 °C led to isoquinolin-1-ylphosphonates 98 in moderate to high yields.

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.