10.1016/S0040-4039(01)02334-6
The research focuses on the microwave-enhanced Goldberg reaction, a novel and efficient method for synthesizing N-arylpiperazinones, N-arylpiperazinediones, and N-aryl-3,4-dihydroquinolinones. The study explores the use of microwave irradiation to accelerate the Goldberg reaction, which traditionally requires harsh conditions, by employing N-methyl-2-pyrrolidinone (NMP) as a solvent. The experiments involved reacting aryl bromides with protected 2-piperazinones or 2,5-piperazinediones under various conditions, with and without microwave irradiation, to optimize reaction rates and yields. Key reactants included bromobenzene, acetanilide, and different polar solvents. The analyses used to determine the success of the reactions and the structures of the products comprised HPLC, NMR, MS, and HRMS techniques. The results demonstrated significant time and energy savings with microwave irradiation, establishing it as a powerful tool in organic synthesis for these transformations.
10.1007/BF00479363
The research focuses on the reaction of N-methyl-2-pyrrolidone and N-methyl-2-piperidone acetals with enamino diketones, aiming to synthesize cyclic dienediamines. The study found that these reactions yield dienediamines, which can be further converted to 3-(8-methylamino)ethyl-6,6-dimethyl-5,6,7,8-tetrahydro-5-coumarinone hydrochloride when heated in dilute hydrochloric acid. Key chemicals used in the process include N,N-dimethylacetamide diethylacetal, aminomethylene- and N,N-dimethylaminomethylenedimedones, and various lactam acetals. The research concluded that the structure of the products depends on the ratio of reagents used, and the synthesized compounds contain a substituted dienediamine fragment, which may have significant effects on the degree of conjugation due to the presence of bulky rings. The study also noted that dienediamine IX and dieneamidino enamine VI are converted to coumarin derivative VIII upon heating in dilute hydrochloric acid.
10.1021/jo00013a049
The research aims to develop a practical and general approach to synthesizing a series of β-(trialkylstannyl)vinyl sulfoxides and sulfones, which are important synthetic intermediates. The study explores alternative methods due to unsatisfactory yields from a literature procedure involving monolithiation and sulfenylation. The researchers discovered an efficient route by reacting sulfenyl chlorides with acetylene, followed by oxidation to obtain sulfoxides and sulfones. They then introduced the trialkylstannyl moiety using hexamethylditin and a palladium catalyst in N-methylpyrrolidinone (NMP), achieving good yields. The conclusions highlight the development of a high-yielding and scalable method for synthesizing these olefinic stannanes, which can be further utilized in Stille couplings to produce functionalized dienes.
10.1016/j.bmc.2010.03.015
The research focuses on the synthesis and anti-HIV activity of alkylated quinoline 2,4-diols, based on naturally occurring quinolone alkaloids, buchapine and compound 2. The study aimed to evaluate their potential as anti-HIV agents in human CD4+ T cell line CEM-GFP, infected with HIV1NL4.3 virus. A series of 45 alkylated derivatives were synthesized and tested for anti-HIV potential. The key intermediates, quinoline 2,4-diol and substituted quinoline 2,4-diol, were synthesized through condensation of aniline or substituted aniline with diethyl malonate under microwave irradiation. The synthesis involved various reactants such as prenyl bromide, K2CO3, DMF, and N-methyl 2-pyrolidone (NMP). The biological evaluation included cytotoxicity testing using an MTT-based cell viability assay and anti-HIV activity determination through p24 antigen capture ELISA. The analyses used included nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared (IR) spectroscopy, high-performance liquid chromatography (HPLC), and elemental analysis to confirm the structure and purity of the synthesized compounds. The study identified several potent inhibitors, with compound 6 showing an IC50 value of 2.35 μM and a therapeutic index better than AZT, the standard anti-HIV drug.
10.3762/bjoc.6.33
The research presents a novel synthetic approach to C3-carbocyclic spirooxindoles using a thermal tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition reaction. The purpose of this study was to develop a concise and efficient method to synthesize densely functionalized spirooxindoles, which are rare structural motifs with potential applications in pharmaceuticals and natural product synthesis. The reaction involves a thermal [3,3]-sigmatropic rearrangement of propargylic acetates to form allenyl acetates, which then undergo a [2 + 2] cycloaddition with an alkyne to produce the desired spirooxindoles. The study concluded that this tandem reaction is highly selective for the distal double bond of the allene, even with densely functionalized substrates, and provides a rapid increase in molecular complexity. The method is tolerant of various functional groups and can be performed in solvents like 1,2-dichlorobenzene or N-methylpyrrolidinone. The research demonstrates a rare example of a thermal [3,3]-sigmatropic rearrangement of a propargylic acetate, expanding the synthetic utility for accessing complex spirooxindole architectures.
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