1532-91-8Relevant academic research and scientific papers
Preparation method of 4-halogenated isoquinoline compound
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Paragraph 0021-0024, (2021/08/19)
The invention relates to a preparation method of a 4-halogenated isoquinoline compound. The method comprises the following steps: adding an Ag2O catalyst, a reactant I, a reactant II, a K2S2O8 oxidant, an acetonitrile solution and magneton into a reactor, placing the reactor in an oil bath pan with the temperature of 60-100 DEG C, heating and reacting for 4-12 hours, pouring the reaction liquid into a separating funnel, adding distilled water, extracting with ethyl acetate, merging the obtained organic phases, carrying out rotary drying by using a rotary evaporator, and carrying out column chromatography separation and purification on a crude product to obtain the 4-halogenated isoquinoline compound, wherein the reactant I is isoquinoline; and the reactant II is KX, and X is halogen. The 4-halogenated isoquinoline compound is synthesized by taking an isoquinoline group as a positioning group and carrying out halogenation reaction at the No.4 site of isoquinoline. The method is mild in reaction condition, relatively high in yield and environment-friendly. Through detection, the synthesized 4-halogenated isoquinoline compound has better biological activity and can be applied to the fields of drug synthesis, pesticide synthesis, paint dye synthesis and the like.
Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes
Fosu, Stacy C.,Hambira, Chido M.,Chen, Andrew D.,Fuchs, James R.,Nagib, David A.
supporting information, p. 417 - 428 (2019/02/14)
Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.
5-Substituted isoquinoline derivatives
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Page 104, (2010/02/10)
A compound represented by the following formula (1) or a salt thereof: wherein R1 represents hydrogen atom, a halogen atom and the like; R2 represents hydrogen atom, a halogen atom, a C1-6 alkyl group and the like; and R3 represents —O—X—C(A1)(A11)—C(A2)(A2l)—N(A3l)(A3)(X represents propylene group etc., A11 and A21 represent hydrogen atom, or a C1-6 alkyl group, A31 represents a C1-6 alkyl group substituted with hydroxyl group, or hydrogen atom, and A1, A2, and A3 represent hydrogen atom, a C1-6 alkyl group and the like) and the like, which has an inhibitory activity on the phosphorylation of myosin regulatory light chain, and is useful for treatment of diseases relating to contraction of various cells and the like.
Heterocyclic Enamides Studies. I. Preparation of 4-Bromo- and 4-Chloroisoquinolines from 1,2-Dihydroisoquinoline Derivatives
Urbanski, Jerzy,Wrobel, Leszek
, p. 417 - 424 (2007/10/02)
The reactions of isoquinoline Reissert compounds analogs 1 with bromine and phosphorus pentachloride as well as the hydrolysis of enamides 1, 2 and 3 have been studied.Compounds 1 treated with bromine in most cases undergo bromination of unsaturated carbon C-4; when treated with PCl5 only 1-phenyl and 1-(2,4,6-trinitrobenzyl) derivatives undergo analogous chlorination.Acidic or basic hydrolysis of starting enamides and their 4-halogeno derivatives results in aromatization with splitting off or retention of substituents at C-1.The sequence of reactions studied can be used as a new interesting route to some 4-bromo or 4-chloroisoquinolines.
PHOTODECARBOXYLATIVE CHLORINATION OF CARBOXYLIC ACIDS VIA THEIR BENZOPHENONE OXIME ESTERS
Hasebe, Masato,Tsuchiya, Takashi
, p. 6287 - 6290 (2007/10/02)
Decarboxylative chlorination of various aromatic and aliphatic carboxylic acids is performed successfully by the photolysis of their benzophenone oxime esters in carbon tetrachloride and corresponding chloro compounds are prepared in good yields.High selective generation of the certain radical and efficiency of the stable radical precursor, benzophenone oxime ester, afford much advantage for radical chemistry.
