260998-77-4Relevant academic research and scientific papers
Photorelease of Pyridines Using a Metal-Free Photoremovable Protecting Group
Dong, Zaizai,Fang, Xiaohong,Kou, Xiaolong,Tan, Weihong,Tang, Xiao-Jun,Wu, Yayun,Zhang, Zhen,Zhao, Rong,Zhou, Wei
, p. 18386 - 18389 (2020)
The photorelease of bioactive molecules has emerged as a valuable tool in biochemistry. Nevertheless, many important bioactive molecules, such as pyridine derivatives, cannot benefit from currently available organic photoremovable protecting groups (PPGs). We found that the inefficient photorelease of pyridines is attributed to intramolecular photoinduced electron transfer (PET) from PPGs to pyridinium ions. To alleviate PET, we rationally designed a strategy to drive the excited state of PPG from S1 to T1 with a heavy atom, and synthesized a new PPG by substitution of the H atom at the 3-position of 7-dietheylamino-coumarin-4-methyl (DEACM) with Br or I. This resulted in an improved photolytic efficiency of the pyridinium ion by hundreds-fold in aqueous solution. The PPG can be applied to various pyridine derivatives. The successful photorelease of a microtubule inhibitor, indibulin, in living cells was demonstrated for the potential application of this strategy in biochemical research.
Phototransposition Chemistry of Methylisothiazoles and Methylthiazoles
Pavlik, James W.,Pandit, Chennagiri R.,Samuel, Christopher J.,Day, A. Colin
, p. 3407 - 3410 (1993)
Methylisothiazoles undergo phototransition in neutral solution to methylthiazoles by a single permutation process.Methylisothiazole -> methylisothiazole transpositions, previously reported to occur, were not detected in these reactions.In trifluoroacetic acid solvent, protonated methylisothiazoles and methylthiazoles phototranspose by P4 and P5 permutation pathways, respectively, resulting in a unique phototransposition cycle.
Preparation method of 2-alkyl substituted thiazole compound
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Paragraph 0047-0050, (2021/06/06)
The invention discloses a preparation method of a 2-alkyl substituted thiazole compound, which comprises the following steps: oxidizing 2-alkyl thiothiazole into 2-alkyl sulfonyl thiazole, mixing the 2-alkyl sulfonyl thiazole with a Grignard reagent, reacting the mixture at 0-5 DEG C, heating the mixture to room temperature to continue the reaction; then adding an acid solution and continuously reacting the components at room temperature to obtain a 2-alkyl substituted thiazole compound, wherein the structural formula of the 2-alkyl thiothiazole is that a Grignard reagent of the 2-alkyl sulfonyl thiazole is RCH2MgX, R1 is selected from C1-C4 alkyl groups, R is selected from H and C1-C4 alkyl groups, and X is halogen. According to the present invention, the use of the expensive palladium catalyst and the ligand is avoided, the use of the poor safety butyl lithium reagent is avoided, the ultra-low temperature of-78 DEG C is not required, the cheap and easily available 2-alkylthiothiazole is adopted as the starting material, the 2-alkyl substituted thiazole compound can be prepared under the milder condition, and the method is suitable for the industrial production.
Palladium catalyzed cross-methylation of bromoheterocycles with intramolecularly stabilized dimethyl indium reagents
Jaber, Nimer,Schumann, Herbert,Blum, Jochanan
, p. 565 - 567 (2007/10/03)
Although the intramolecularly stabilized [(3- dimethylamino)propyl]dimethylaluminum (1a) fails to undergo palladium-catalyzed cross-coupling with bromopyridines and with bromofuran derivatives, the analogous gallium and indium reagent lb and 1c smoothly c
