626-55-1Relevant articles and documents
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
supporting information, p. 18386 - 18389 (2020/08/24)
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.
Synthesis method of 3-bromopyridine
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Paragraph 0017-0024, (2020/05/05)
The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 3-bromopyridine. The synthesis method comprises the following steps: (1) dropwise adding bromine into pyridine and 80-95% sulfuric acid at 0 DEG C, and reacting at 130-140 DEG C for 7-8 hours; (2) after the reaction is finished, cooling, pouring into ice water, and regulating the pH value to8 by using 6N sodium hydroxide; and (3) extracting with an organic solvent, layering, drying, filtering, concentrating and distilling. The method has the beneficial effects of high yield, mild reaction conditions, simple reaction steps and simple and easily available raw materials, and is suitable for industrial production.
Implementing Hydrogen Atom Transfer (HAT) Catalysis for Rapid and Selective Reductive Photoredox Transformations in Continuous Flow
Steiner, Alexander,Williams, Jason D.,Rincón, Juan A,de Frutos, Oscar,Mateos, Carlos,Kappe, C. Oliver
supporting information, p. 5807 - 5811 (2019/08/01)
The reductive transformation of aryl halides and carbonyl compounds is a key step in many photoredox transformations. By combining a highly reducing organic photocatalyst with a thiol hydrogen atom transfer (HAT) catalyst, we showcase rapid and highly selective reactions of these synthetically important starting materials in continuous flow. The fast reduction of aryl iodides, bromides and chlorides has been demonstrated with residence times in some cases below one minute. Selectivity between mono- and di-dehalogenation could also be achieved in some cases. Aryl ketones, aldehydes and imines were shown to undergo facile pinacol couplings, and the coupling of an aryl chloride with a styrene was also successful.