15765-17-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,4(1H,3H)-Pyrimidinedione, 1-ethenylis utilized as a precursor in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical structure allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Polymer and Coating Production:
Vinylbarbituric acid is also employed in the production of polymers and coatings, where its chemical properties contribute to the desired characteristics of the final products, such as durability and stability.
Used in Medical Applications:
2,4(1H,3H)-Pyrimidinedione, 1-ethenylis known for its sedative and hypnotic properties. It is used in the medical field for the treatment of insomnia and anxiety disorders, providing relief to patients suffering from sleep disturbances and stress-related conditions.

Upstream product

• 66-22-8 uracil 
• 74-86-2 acetylene 
• 15816-10-1 1-(2-chloroethyl)uracil 
• 108-05-4 vinyl acetate 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 936-70-9 1-(2-hydroxyethyl)-uracil 

Downstream Products

• 1080634-13-4 1-{(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazol-2-yl}uracil 
• 1080634-14-5 1-{(2S,3aS,4R,5R,6R)-4,5-bis(benzyloxy)-6[(benzyloxy)methyl]hexahydropyrrolo[1,2-b]isoxazol-2-yl}uracil 
• 391198-86-0 (+/-)-1-(2'-H-1',2'-isoxazolidin-5'-yl)-4-(4-nitrophenoxy)-pyrimidin-2-(1H)-one 
• 627485-66-9 1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonyl-1,2-isoxazolidin-5-yl]-1H-pyrimidine-2,4-dione 
• 557794-49-7 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-1H-pyrimidine-2,4-dione 
• 557794-47-5 1-[(5S)-2-{(3aR,4R,6R,6aR)-6-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-1,2-oxazolidin-5-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione 

Relevant academic research and scientific papers

Nucleoside Analogues: Synthesis from Strained Rings

Nucleoside analogues are widely employed as bioactive compounds against cancer and viral infections. Consequently, it is important to develop efficient synthetic methods to access them with high efficiency and structural diversity. Herein, we present a full account of our work on the synthesis of nucleoside analogues via annulations of donor acceptor aminocyclopropanes and aminocyclobutanes. Thymine- and uracil-derived diester cyclopropanes were accessed from the corresponding nucleobases via vinylation and rhodium-catalyzed cyclopropanation, and were then used in (3+2) annulations with aldehydes, ketones and enol ethers. The obtained analogues could be transformed into important hydroxymethyl derivatives. Thymine and fluoro-uracil-derived diester cyclobutanes obtained from the nucleobases via vinylation and (2+2) cycloaddition could also be used in a (4+2) annulation with aldehydes. Finally, purine-derived diester cyclopropanes could be accessed using the condensation of nucleobases with chloromethyl ethylidene malonates, but annulation reactions with this class of substrates were not successful.

Synthesis of dihydroisoxazole nucleoside and nucleotide analogs

The dihydroisoxazole nucleosides as well as their phosphonate derivatives were efficiently prepared via 1,3-dipolar cycloaddition reactions of nitrile oxides with corresponding vinyl nucleoside bases for antiviral studies.

Synthesis of (Carbo)nucleoside analogues by [3+2] annulation of aminocyclopropanes

(Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-acceptor cyclopropanes and their use in the indium- and tin-catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products could be easily decarboxylated and reduced to the corresponding alcohols. The method gives access to a broad range of new (carbo)nucleoside analogues in only four or five steps and will be highly useful for the synthesis of libraries of bioactive compounds.

A convenient method for the synthesis of N-vinyl derivatives of nucleobases

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) reveals, one more time, its enormous flexibility as Lewis acid catalyst, transforming the well known, but drastic, exchange of the acetyl group of vinyl acetate with pyrimidine and purine derivatives in a very gentle and quick method to obtain a whole set of vinyl nucleobases.

A short synthesis of 1-vinyluracil and 1-vinylthymine

1-Vinyluracil and 1-vinylthymine, monomers for nucleic acid bases attached functional polymers, were synthesized for the first time from uracil and thymine in 3 steps in 54% and 50% overall yields using the Mitsunobu reactions of 2a and 2b with 2-chloroet