130-16-5Relevant articles and documents
Nonreductive deiodination of ortho-iodo-hydroxylated arenes using tertiary amines
Talekar, Rahul Subhash,Chen, Grace Shiahuy,Lai, Shin-Yu,Chern, Ji-Wang
, p. 8590 - 8593 (2005)
A convenient and nonreductive deiodination is reported for the ortho-iodo-hydroxylated arenes inch ding derivatives of quinolinol, phenol, and naphthol. Tertiary amines pyridine, triethylamine, and N-methylmorpholine in the presence of water initiated deiodination of ortho-iodo-hydroxylated arenes without affecting para-iodine and other reduction-susceptible groups. This reported method also works efficiently for polyiodinated systems. Simplicity, short reaction times, and absence of reducing catalyst are features of this method.
A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines
Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake
, p. 1782 - 1788 (2018/02/23)
An operationally simple and metal-free protocol for geometrically inaccessible C5-H halogenation of a range of 8-substituted quinoline derivatives has been established. The reaction proceeds under air, with inexpensive and atom economical trihaloisocyanuric acid as a halogen source (only 0.36 equiv.), at room temperature. Exceptionally high generality with respect to quinoline is observed, and in most instances, the reaction proceeded with complete regioselectivity. Quinoline with a variety of substituents at the 8-position gave, exclusively, the C5-halogenated product in good to excellent yields. Phosphoramidates, tertiary amides, N-alkyl/N,N-dialkyl, and urea derivatives of quinolin-8-amine as well as alkoxy quinolines were halogenated at the C5-position via remote functionalization for the first time. This methodology provides a highly economical route to halogenated quinolines with excellent functional group tolerance, thus providing a good complement to existing remote functionalization methods of quinolin-8-amide derivatives and broadening the field of remote functionalization. The utility of the method is further showcased through the synthesis of several compounds of biological and pharmaceutical interest.
Preparation method of 5-chloro-8-hydroxyquinoline
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Paragraph 0040; 0041; 0049; 0051; 0053; 0055, (2018/07/15)
The invention discloses a preparation method of 5-chloro-8-hydroxyquinoline, aiming at solving the problems that when the 5-chloro-8-hydroxyquinoline is prepared by using 4-chloro-2-aminophenol, 4-chloro-2-nitrophenol and glycerol as raw materials and adopting a Skraup method in a loop closing way at present, sulfuric acid reacts violently with the glycerol in a process of dropwise adding the sulfuric acid so as to produce a large amount of acrolein, the acrolein self-polymerizes into tar, the tar is not only difficult to remove during the post-treatment of the product, but also reduces the reaction yield, the reaction process is difficult to control, and a great deal of waste acid is produced. According to the preparation method, hydrochloric acid is used as a solvent and the acrolein istaken as a loop closing raw material, so that the step of producing the acrolein by using the sulfuric acid and the glycerol is avoided, the generation of the tar is effectively reduced, and the heatrelease state of the reaction is controlled; furthermore, the problem that impurities are produced due to a sulfonation reaction of the product can be avoided, the product yield and safety are improved, the reaction is easy to control, and industrialization is easily realized; therefore, the preparation method has a higher application value.