Convenient synthesis of arylpropargyl aldehydes and 4-aryl-3-butyn-2-ones from arylacetylenes and amide acetals

The reaction of arylacetylenes 1 and N,N-dimethylformamide dimethylacetal (2a, DMF-DMA) afforded the corresponding arylpropargyl aldehydes 3 in moderate yields. Similarly, the reaction of 1 and N,N-dimethylacetamide dimethylacetal (2b, DMA-DMA) gave 4-aryl-3-butyn-2-ones 4.     

Design,synthesis, and biological evaluation of indolylidinepyrazolones as potential anti-bacterial agents

A series of indolylidinepyrazolones were synthesized using a simple, green, and effective route and evaluated as anti-bacterial agents. The compounds were further studied via structure-guided docking study. One of the compounds exhibiting H-bonding interactions with conserved residue Arg144 turned out to be the most potent compound of the series. The minimum inhibitory concentration values ranged from 50 to 25 μg/mL against Staphylococcus aureus in their anti microbial evaluation.     

萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成

研究了萘基薁并[2,1-d]嘧啶-4-胺类衍生物的合成方法.以托酚酮、萘乙酸乙酯、N,N-二甲基甲酰胺二甲缩醛(DMF-DMA)及芳香胺为原料,依次经过氯代、缩合、环加成、环化反应得到目标产物.该反应操作简单、条件温和、收率良好.产物的结构经1H NMR,IR及元素分析等得以证实.     

Green synthesis of novel (E)-2-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-2-carbonyl)-3-(1H-indol-3-yl)acrylonitriles

Green synthesis of novel title compounds (6) has been developed from 3-(1,4-dioxo-3,4-dihydrophthalazin-(1H)-yl)-3-oxopropanenitrile (3) and indole-3-aldehyde (4) using Knoevenagel condensation followed by alkylation with alkylating agents. Compound 6 could also be synthesised by alkylation of 4 followed by condensation with 3. In an alternate sequence of reactions, 6 could be synthesised either from treatment of 3 with N,N-dimethylformamide dimethyl acetal to form (E)-3-(dimethlamino)-2-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-2-carbonyl)acrylonitrile 8 followed by reaction with 10 or by the reaction 8 with 9 followed by alkylation.     

Vinylogous N,N-dimethylaminomethylenation of 3-[(1-substituted)ethylidene]-oxindoles with N,N-dimethylformamide dimethylacetal

An efficient stereoselective synthesis of various 3-(3-dimethylaminoprop-2-enylidene)oxindoles has been disclosed. The compounds were synthesized via a vinylogous N,N-dimethylaminomethylenation at the γ-position of 3-[(1-substituted)ethylidene]oxindoles with DMF-DMA.     

Search for evidence of life in space: Analysis of enantiomeric organic molecules by N,N-dimethylformamide dimethylacetal derivative dependant Gas Chromatography–Mass Spectrometry

Within the context of the future space missions to Mars (MSL 2011 and Exomars 2016), which aim at searching for traces of life at the surface, the detection and quantitation of enantiomeric organic molecules is of major importance. In this work, we have developed and optimized a method to derivatize and analyze chiral organic molecules suitable for space experiments, using N,N-dimethylformamide dimethylacetal (DMF-DMA) as the derivatization agent. The temperature, duration of the derivatization reaction, and chromatographic separation parameters have been optimized to meet instrument design constraints imposed upon space experiment devices. This work demonstrates that, in addition to its intrinsic qualities, such as production of light-weight derivatives and a great resistance to drastic operating conditions, DMF-DMA facilitates simple and fast derivatization of organic compounds (three minutes at 140 °C in a single-step) that is suitable for an in situ analysis in space. By using DMF-DMA as the derivatization agent, we have successfully identified 19 of the 20 proteinic amino acids and been able to enantiomerically separate ten of the potential 19 (glycine being non-chiral). Additionally, we have minimized the percentage of racemized amino acid compounds produced by optimizing the conditions of the derivatization reaction itself. Quantitative linearity studies and the determination of the limit of detection show that the proposed method is also suitable for the quantitative determination of both enantiomeric forms of most of the tested amino acids, as limits of detection obtained are lower than the ppb level of organic molecules already detected in Martian meteorites.