An efficient synthesis of 1,3-disubstituted 5-diethoxyphosphoryluracils

Pięta, Marlena; Kędzia, Jacek; Janecki, Tomasz

doi:10.1016/j.tetlet.2015.02.094

Cited by 5 publications

(1 citation statement)

References 17 publications

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“…The amide 732 is converted into the intermediary 734 by thermal treatment with N , N -dimethylformamide-dimethyl acetal 733 . Then, 734 is treated with an aliphatic or aromatic amine 735 at room temperature to afford the corresponding amino-amide 736 , which finally is converted to the uracil derivative 731 after cyclization in the presence of phosgene …”

Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search in the development of synthetic routes for obtaining novel members of this family of compounds. This updated review covers methodologies established since 2004, focusing on the synthesis of azaheterocyclic phosphonates, of which the phosphonate moiety is directly substituted onto to the azaheterocyclic structure. Emphasizing recent advances, this review classifies newly developed synthetic approaches according to the ring size and providing information on biological activities whenever available. Furthermore, this review summarizes information on various methods for the formation of C–P bonds, examining sustainable approaches such as the Michaelis–Arbuzov reaction, the Michaelis–Becker reaction, the Pudovik reaction, the Hirao coupling, and the Kabachnik–Fields reaction. After analyzing the biological activities and applications of azaheterocyclic phosphonates investigated in recent years, a predominant focus on the evaluation of these compounds as anticancer agents is evident. Furthermore, emerging applications underline the versatility and potential of these compounds, highlighting the need for continued research on synthetic methods to expand this interesting family.

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Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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ChemInform Abstract: An Efficient Synthesis of 1,3‐Disubstituted 5‐Diethoxyphosphoryluracils.

2015

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An Efficient Synthesis of 1,3-Disubstituted 5-Diethoxyphosphoryluracils. -Sequential reaction of diethylphosphoryl acetamides with acetal (II), and amines followed by cyclization in the presence of phosgene affords the title compounds in good yields. -(PIETA, M.; KEDZIA, J.; JANECKI*, T.; Tetrahedron Lett. 56 (2015) 14, 1891-1893, http://dx.doi.org/10.1016/j.tetlet.2015.02.094 ; Inst. Org. Chem., Tech. Univ., PL-90-924 Lodz, Pol.; Eng.) -Mais 30-224

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Enantioselective synthesis of 5-methylidenedihydrouracils as potential anticancer agents

et al. 2019

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An efficient synthesis of 1,3-disubstituted 5-diethoxyphosphoryluracils

Cited by 5 publications

References 17 publications

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

ChemInform Abstract: An Efficient Synthesis of 1,3‐Disubstituted 5‐Diethoxyphosphoryluracils.

Enantioselective synthesis of 5-methylidenedihydrouracils as potential anticancer agents

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