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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.


FeCl3-catalyzed four-component reaction for the synthesis of 1,5-benzodiazepin-2-ylphosphonates.
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C28: FeCl3-catalyzed four-component reaction for the synthesis of 1,5-benzodiazepin-2-ylphosphonates.

Mentions: The second method comprises a one-pot four-component reaction of diamines 130, ketones 131 and phosphites 132 in the presence of FeCl3 as a catalyst to give benzodiazepinylphosphonates 133 and 134 and has been reported by Bhattacharya et al. (Scheme 28) [54]. The authors observed that the presence of molecular sieves (4 Å) had a beneficial effect on the yield of the reaction due to trapping of water resulting from the imine formation reaction. The generality of the reaction has been investigated by the use of structurally diverse diamines, ketones and phosphonates. While the reaction proceeded well with different amines and phosphonates, only the use of acetone as the ketone component afforded the corresponding benzodiazepinylphosphonates. With other ketones only ketimine intermediates were obtained which were sterically too crowded for attacking the phosphorus atom of the phosphonates. The use of unsymmetrically substituted diamines led to the corresponding syn-regioisomers as the major product and the anti-regioisomer as the minor product. Some of the synthesized 1,5-benzodiazepin-2-ylphosphonates showed cysteine protease inhibition activities.


Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates
FeCl3-catalyzed four-component reaction for the synthesis of 1,5-benzodiazepin-2-ylphosphonates.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

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

C28: FeCl3-catalyzed four-component reaction for the synthesis of 1,5-benzodiazepin-2-ylphosphonates.
Mentions: The second method comprises a one-pot four-component reaction of diamines 130, ketones 131 and phosphites 132 in the presence of FeCl3 as a catalyst to give benzodiazepinylphosphonates 133 and 134 and has been reported by Bhattacharya et al. (Scheme 28) [54]. The authors observed that the presence of molecular sieves (4 Å) had a beneficial effect on the yield of the reaction due to trapping of water resulting from the imine formation reaction. The generality of the reaction has been investigated by the use of structurally diverse diamines, ketones and phosphonates. While the reaction proceeded well with different amines and phosphonates, only the use of acetone as the ketone component afforded the corresponding benzodiazepinylphosphonates. With other ketones only ketimine intermediates were obtained which were sterically too crowded for attacking the phosphorus atom of the phosphonates. The use of unsymmetrically substituted diamines led to the corresponding syn-regioisomers as the major product and the anti-regioisomer as the minor product. Some of the synthesized 1,5-benzodiazepin-2-ylphosphonates showed cysteine protease inhibition activities.

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.