38018-27-8

Usage

Uses

Used in Organic Synthesis:
(1-but-3-ynyl)pyrrolidine-2,5-dione is used as a versatile intermediate in organic synthesis for its ability to undergo various reactions, including addition, substitution, and condensation. This allows for the formation of a wide range of organic compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (1-but-3-ynyl)pyrrolidine-2,5-dione is used as a key building block for the synthesis of various pharmaceuticals. Its unique reactivity contributes to the development of new and innovative drugs.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, (1-but-3-ynyl)pyrrolidine-2,5-dione is utilized as an important intermediate for the synthesis of agrochemicals, such as pesticides and herbicides, due to its potential to form a diverse array of compounds.
It is crucial to handle (1-but-3-ynyl)pyrrolidine-2,5-dione with care, as it can be hazardous if not properly used and stored. Proper safety measures and storage conditions are essential to ensure the safe utilization of (1-but-3-ynyl)pyrrolidine-2,5-dione in various applications.

Upstream product

• 123-56-8 Succinimide 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 88695-24-3 1-((Z)-4-Benzenesulfinyl-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione 
• 92845-41-5 1-((Z)-4-Phenylsulfanyl-4-trimethylsilanyl-but-3-enyl)-pyrrolidine-2,5-dione 
• 38018-23-4 N-But-3-ynyl-succinamic acid 
• 927-74-2 3-Butyn-1-ol 

Downstream Products

• 88695-25-4 1-((E)-4-Benzenesulfinyl-but-3-enyl)-pyrrolidine-2,5-dione 
• 1060671-56-8 1-{2-[1-(toluene-4-sulphonyl)-1H-indol-2-yl]ethyl}pyrrolidine-2,5-dione 
• 58805-02-0 hexahydroindolizine-3,7-dione 
• 144252-30-2 7-pyrrolido<2,1-b>-2-methyl-3-(phenylthiomethyl)-2,3,4,5-tetrahydro-<1,3>oxazepine 
• 58804-96-9 1-(3-butynyl)-5-ethoxy-2-pyrrolidinone 

Relevant academic research and scientific papers

Synthesis of succinimidoalkylbenzaldehyde analogues: Potential bifunctional linkers for bioconjugation

A series of novel 4-substituted benzaldehydes containing a succinimide moiety were synthesized as potential bifunctional linkers for the purpose of binding therapeutic drugs to antibodies raised against cancer cells. These potential benzaldehyde linkers varied in the nature of the para functionality so as to provide a range of potential acid labilities. Synthesis of the linkers involved a Williamson ether formation to make the ether linker 1, a Sonagoshira palladium-catalyzed coupling to synthesize the skeleton of the alkyl linker 2, and formation of an amide bond directly from a methyl ester gave the 4-substituted amide linker 3. As an example of the type of acetal that can be produced using these linkers, uridine was used as an analogue of the cytotoxic compound 5-fluorouridine to give the cyclic acetals 19?21. CSIRO 2008.

Silylstannylation of allenes and silylstannylation-cyclization of allenynes. Synthesis of highly functionalized allylstannanes and carbocyclic and heterocyclic compounds

Catalyzed by Pd(0), trialkylsilyltrialkylstannane (R3Si- SnR′3) reagents undergo highly selective additions to 1,2-dien-7-ynes and 1,2-dien-8-ynes to give 2-vinylalkylidenecyclopentanes with silicon and tin substituents on the double bonds. Similar additions of distannanes and borostannanes show that the reactions with silylstannanes are superior in terms of ease of handling of the bifunctional reagents and the isolation of the products after the reaction. The chemo- and regioselectivities are controlled by the enhanced reactivity of the allene unit, while the (Z)-geometry of the exocyclic stannylvinylidene is a consequence of the syn-carbometalation and subsequent reductive elimination from Pd with retention of configuration at the vinyl carbon. Synthesis of highly functionalized pyrrolidines and indolizidines and the reluctance of certain kinds of allenynes and silicon-tin reagents to undergo the cyclization illustrate the scope and limitations of the reaction. Based on the isolation of intermediates, a mechanism for the formation of the cyclic compounds is proposed. Model transition states to explain the stereoselectivity in cyclization of substituted allenynes are provided. Further elaboration using the vinyltin and vinylsilane moieties should lead to highly functionalized carbocyclic and heterocyclic compounds. Under similar conditions, addition of silylstannanes to highly functionalized allenes gives E-allylstannanes with high stereoselectivity. Functional groups such as THP- and silyl-ethers, lactones, β- and γ-lactams, α,β-unsaturated esters, olefins, and substituted acetylenes are tolerated under the reaction conditions.

Model studies for damage to nucleic acids mediated by thiyl radicals

The ability of phenylthiovinyl radicals to abstract hydrogen from appropriately substituted carbon atoms has been studied as a model for the reactions of the deoxyribose units of DNA with similar radicals in two.

A practial method for N-alkylation of succinimide and glutarimide

Succinimide and glutarimide are N-alkylated in high yield using primary chlorides, bromides or tosylates under solid-liquid PTC conditions (K2CO3, benzene or toluene at reflux, 1percent 18-C-6).Addition of 0.1 eq of KI increases the rate of the reaction for less reactive halides such as 2-bromobutane.Keywords: imide / phase transfer catalysis / N-alkylation

SILA-PUMMERER REARRANGEMENTS AT SP2-HYBRIDIZED CARBON

α-Trimethylsilylvinyl sulfoxides undergo sila-Pummerer rearrangements upon warming in benzene.Alkynes, vinylsulfoxides, and ketene S,O-acetals are obtained as products.

α-ACYLIMINIUM ION-ACETYLENE CYCLISATIONS

Cyclisation of acetylenic ethoxylactams 1b-12b leads to bridgehead nitrogen bicyclic ketones in excellent yields.The reaction is weakly acid-catalysed and proceeds at ambient temperature.The observed regioselectivity effect is discussed in terms of stability of exo vs endo vinyl cations and ring strain effects.The high yield conversion of N-(5-hexynyl)-ethoxy lactams 7b and 8b in the 5/8 and 6/8 fused bicyclic ketolactams 7c and 8c deserves special attention.