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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.


Synthesis of 1,5-benzodiazepin-2-ylphosphonates via ytterbium chloride-catalyzed three-component reaction.
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C27: Synthesis of 1,5-benzodiazepin-2-ylphosphonates via ytterbium chloride-catalyzed three-component reaction.

Mentions: 2.2.8 Benzodiazepinylphosphonates: There are only two publications related to the multicomponent synthesis of benzodiazepinylphosphonates in the literature. Both syntheses are based on o-diaminobenzene as the starting material. In the first method, an YbCl3-catalyzed three-component reaction between an o-diaminobenzene 124, 2,4-pentanedione (125) and diethyl phosphite under optimized solvent-free conditions (10 mol % of YbCl3, 22 °C, 1:1:1 molar ratio of starting materials) afforded 1,5-benzodiazepin-2-ylphosphonates 126 in moderate yields (Scheme 27) [53]. The undesired diphosphonate 127 was formed in 1:1:2 or 1:1:4 molar ratio of o-diaminobenzene 124, 1,3-butanediones 125 and diethyl phosphite. When butanediones 128 with a larger substituent than Me were used, only monophosphonates 129 were obtained.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
Synthesis of 1,5-benzodiazepin-2-ylphosphonates via ytterbium chloride-catalyzed three-component reaction.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C27: Synthesis of 1,5-benzodiazepin-2-ylphosphonates via ytterbium chloride-catalyzed three-component reaction.
Mentions: 2.2.8 Benzodiazepinylphosphonates: There are only two publications related to the multicomponent synthesis of benzodiazepinylphosphonates in the literature. Both syntheses are based on o-diaminobenzene as the starting material. In the first method, an YbCl3-catalyzed three-component reaction between an o-diaminobenzene 124, 2,4-pentanedione (125) and diethyl phosphite under optimized solvent-free conditions (10 mol % of YbCl3, 22 °C, 1:1:1 molar ratio of starting materials) afforded 1,5-benzodiazepin-2-ylphosphonates 126 in moderate yields (Scheme 27) [53]. The undesired diphosphonate 127 was formed in 1:1:2 or 1:1:4 molar ratio of o-diaminobenzene 124, 1,3-butanediones 125 and diethyl phosphite. When butanediones 128 with a larger substituent than Me were used, only monophosphonates 129 were obtained.

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.