- Method for preparing 1-cyclopropylnaphthalene
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The invention belongs to the technical field of organic synthesis, and particularly discloses a method for preparing 1-cyclopropylnaphthalene. According to the method disclosed by the invention, 1-naphthylacetophenone is adopted as a raw material, and 1-cyclopropylnaphthalene can be simply and conveniently synthesized through reduction, dehydration, cyclization and reductive dehalogenation. The method has the advantages of cheap and easily available raw materials, no need of precious metals or dangerous organic metal reagents, low raw material cost, convenient production, environmental protection and safety, and is very suitable for industrial production. The method disclosed by the invention has the advantages of high yield in each step, few byproducts and easiness in purification.
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Paragraph 0044-0046; 0054-0055; 0056-0058; 0063; 0064; ...
(2021/07/09)
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- Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents
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Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C?C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp2?Csp3 coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide-substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram-scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.
- Dilchert, Katharina,Gessner, Viktoria H.,Gro?johann, Angela,Rodstein, Ilja,Scherpf, Thorsten,Steinert, Henning,Tappen, Jens
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supporting information
p. 20596 - 20603
(2020/09/09)
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- Method for synthesizing aromatic compound by coupling palladium/imidazole salt with nitroaromatic hydrocarbon and boric acid compound (by machine translation)
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The invention discloses a method, for coupling a palladium/imidazole salt with a nitroaromatic hydrocarbon and a boric acid compound to synthesize an aromatic compound. The method comprises: in organic solvent, taking nitroaromatic hydrocarbon and boric acid compound as substrate, palladium/imidazole salt as a catalyst, carrying out coupling reaction under the action of alkali, and carrying out post-treatment to obtain the aromatic compound. The method is simple, easy to store, low in price, relatively low in ligand consumption, high in product yield, good in substrate applicability, and suitable for alkyl boronic acid. The process of the invention can be used to synthesize a series of aromatic compounds, for example. The compound has wide application value in the fields of pesticides, medicines, materials and the like. (by machine translation)
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Paragraph 0154-0158
(2019/10/01)
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- Sterically hindered N-heterocyclic carbene/palladium(ii) catalyzed Suzuki-Miyaura coupling of nitrobenzenes
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Palladium-catalyzed denitrative Suzuki coupling of nitroarenes using 2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the ligands is described. The key to success is the use of the NHC ligands which show strong donating ability and suitable steric hindrance allowing the successful oxidative addition of Ar-NO2 bonds. Both aromatic and aliphatic boronic acids are tolerated, and a variety of biphenyls and alkylarenes were obtained in good to excellent yields.
- Chen, Kai,Chen, Wei,Yi, Xiaofei,Chen, Wanzhi,Liu, Miaochang,Wu, Huayue
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supporting information
p. 9287 - 9290
(2019/08/08)
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- Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes
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The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.
- Sinha, Narayan,Heijnen, Dorus,Feringa, Ben L.,Organ, Michael G.
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supporting information
p. 9180 - 9184
(2019/07/04)
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- Lesinurad analogue and its preparation method and medical use
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The invention relates to a lesinurad analog as shown in the general formula (I), its preparation method, a pharmaceutical composition containing the derivative and an application of the pharmaceutical composition used as a therapeutic agent, especially as a medicine for treating hyperuricemia and gout, wherein definition of each substituent group in the general formula (I) is as the same as definition in the specification.
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Paragraph 0046; 0047; 0049; 0050
(2019/05/28)
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- Naphthyl thiocarbonyl compound as well as preparation method and application thereof
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The invention provides a naphthyl thiocarbonyl compound of a structural formula I. The invention further provides a preparation method of the compound and application of the compound in preparation ofa lesinurad key intermediate 1-cyclopropylnaphthalene-4-benzyl isothiocyanate of a structural formula VII. The structural formula is as shown in the specification. In the formula, R represents hydroxyl or thio.
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Paragraph 0100; 0101; 0102; 0103
(2019/04/13)
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- Preparation method of 1-cyclopropyl naphthalene
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The invention discloses a preparation method of 1-cyclopropyl naphthalene. The method comprises the following steps: carrying out a ring closing reaction on a compound 1, shown in a formula describedin the description, under the acidic condition so as to obtain 3-(1-naphthyl)dihydrofuran-2(3H)-one; enabling the 3-(1-naphthyl)dihydrofuran-2(3H)-one to form cyclopropyl under the alkaline conditionso as to obtain the 1-cyclopropyl naphthalene. The preparation method provided by the invention solves a series of problems that in the production of the 1-cyclopropyl naphthalene, the reaction conditions are harsh, the reaction causes pollution, the reaction hazardous degree is high, scale-up production is not easily realized, and the like.
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Paragraph 0027-0032
(2019/01/14)
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- PROCESS FOR MANUFACTURING 1-CYCLOPROPYL-NAPHTHALENES
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A process for preparing 1-cyclopropyl-naphthalene derivatives of Formula (1) wherein R1-R7 are independently hydrogen, alkyl, alkoxy, cycloalkyl or aryl comprising the steps of a) contacting an acid salt of a 1-naphthyl-2-aminoethylketone with a base and a first solvent to obtain a solution wherein the molar ratio of base to l-naphthyl-2-aminoethylketone acid salt is at least 0.7, b) addition of hydrazine to obtain a 3-(1-naphthyl)-1H-pyrazoline, c) optionally adding a second solvent and/or at least partially removing the first solvent, and d) heating the reaction mixture to a temperature above 190°C to obtain the compound of Formula (1).
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Page/Page column 9; 10
(2017/01/31)
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- Aryl/heteroaryl pentafluorobenzenesulfonates (ArOPFBs): New electrophilic coupling partners for room temperature Suzuki-Miyaura cross-coupling reactions
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The first cross-coupling reaction between aryl/heteroaryl pentafluorobenzenesulfonates and aryl/heteroaryl boronic acids under mild conditions is described. The successful synthesis of highly ortho substituted biaryls and high chemoselectivity of these bench stable intermediates over tosylates, triflates, mesylates, and chlorides increases its scope as a valuable cross-coupling partner. The generality of this protocol was further extended to other boron containing nucleophiles (boronates, trifluoroborates) and alkyl boronic acids.
- Joseph, Jayan T.,Sajith, Ayyiliath M.,Ningegowda, Revanna C.,Nagaraj, Archana,Rangappa,Shashikanth, Sheena
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supporting information
p. 5106 - 5111
(2015/08/06)
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- MANUFACTURE OF 2- (5- BROMO-4 (-CYCLOPROPYLNAPHTHALEN-1-YL) -4H-1,2,4-TRIAZOL-3-YLTHIO) ACETIC ACID
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Described herein are certain processes for the synthesis of compounds of Formula (I):
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Paragraph 0345-0348
(2014/01/18)
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- Facile synthesis of aryl(het)cyclopropane catalyzed by palladacycle
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Sphos (2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′- biphenyl) adduct of cyclopalladated ferrocenylimine (IIe) exhibited highly catalytic activity for the Suzuki cross-coupling reaction of cyclopropylboronic acid with aryl(het) halides with 1 mol % catalyst loading. This process was applied to both of aryl and heteroaryl halides (Br and Cl), and made the various arylcyclopropane and heteroarylcyclopropane to be easily synthesized. A variety of substituents on the aryl halides, such as alkyl, acetyl, benzoyl, ether, formyl, carboxylate, methoxy, nitro and cyano were tolerated.
- Zhang, Min,Cui, Xiuling,Chen, Xiaopei,Wang, Lianhui,Li, Jingya,Wu, Yusheng,Hou, Lifen,Wu, Yangjie
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experimental part
p. 900 - 905
(2012/02/01)
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- Cross-coupling of mesylated phenol derivatives with potassium cyclopropyltrifluoroborate
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C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%. (Figure presented)
- Molander, Gary A.,Beaumard, Floriane,Niethamer, Terren K.
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experimental part
p. 8126 - 8130
(2011/11/12)
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- POLYMORPHIC, CRYSTALLINE AND MESOPHASE FORMS OF SODIUM 2-(5-BROMO-4-(4-CYCLOPROPYLNAPHTHALEN-1-YL)-4H-1,2,4-TRIAZOL-3-YLTHIO)ACETATE, AND USES THEREOF
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Crystalline polymorphs and solid mesophase forms of sodium 2-(5-bromo-4- (4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-ylthio)acetate are described. In addition, pharmaceutical compositions and uses of such compositions for the treatment of a variety of diseases and conditions are provided.
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Page/Page column 36
(2011/08/03)
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- NOVEL COMPOUNDS AND COMPOSITIONS AND METHODS OF USE
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Described herein are compounds useful in the modulation of blood uric, acid levels, formulations containing them and methods of using them. In some embodiments, the compounds described herein are used in the treatment or prevention of disorders relafed to aberrant levels of uric acid
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Page/Page column 89
(2009/07/03)
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- Lanthanum metal-assisted cyclopropanation of alkenes with gem-dihaloalkanes
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It was confirmed that lanthanum metal was an efficient reagent for the reductive dehalogenation of gem-dihaloalkanes. When gem-dihaloalkanes were allowed to react with lanthanum metal in the presence of alkenes, cyclopropanation of the alkenes occurred under mild conditions giving the corresponding cyclopropanes in moderate to good yields.
- Nishiyama, Yutaka,Tanimizu, Hana,Tomita, Tsuyoshi
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p. 6405 - 6407
(2008/02/12)
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- Suzuki coupling of cyclopropylboronic acid with aryl halides catalyzed by a palladium-tetraphosphine complex
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The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)- cyclopentane (Tedicyp) in combination with [Pd(C3H 5)Cl]2 affords a very efficient catalyst for the coupling of cyclopropylboronic acid with aryl bromides and aryl chlorides. Higher reactions rates were observed with aryl bromides than with aryl chlorides; however, even in the presence of 1-0.4% of catalyst, a few aryl chlorides gave the coupling products in good yields. A wide variety of substituents such as alkyl, methoxy, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, and nitrile on the aryl halides are tolerated. The coupling reaction of sterically very congested aryl bromides such as bromomesitylene or 2,4,6-triisopropylbromobenzene also proceeds in good yields. Copyright Taylor & Francis LLC.
- Lemhadri, Mhamed,Doucet, Henri,Santelli, Maurice
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p. 121 - 128
(2007/10/03)
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- S-TRIAZOLYL α-MERCAPTOACETANILDES AS INHIBITORS OF HIV REVERSE TRANSCRIPTASE
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A series of S-triazolyl α-mercaptoacetanilides having general structure (1) are provided, where Q is CO2H, CONR2, SO3H, or SO2NR2. The compounds inhibit several variants of the reverse transcriptase of HIV, and are useful in the treatment of HIV infections.
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Page/Page column 20
(2010/10/20)
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