- Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis
-
The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.
- Wang, Jian,Li, Yan-Hui,Pan, Song-Cheng,Li, Ming-Fang,Du, Wenting,Yin, Hong,Li, Jing-Hua
-
supporting information
p. 146 - 153
(2020/03/10)
-
- Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions
-
A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.
- Zhang, Xitao,Feng, Xiujuan,Zhang, Haixia,Yamamoto, Yoshinori,Bao, Ming
-
supporting information
p. 5565 - 5570
(2019/10/22)
-
- Environment-friendly preparation method of 2-chloroquinoline
-
The invention discloses an environment-friendly preparation method of 2-chloroquinoline. The method comprises the following steps: dissolving quinoline N-oxide as a raw material in a certain amount ofa solvent, adding inorganic salt, a cocatalyst, organic alkali and a phase transfer catalyst to form a raw material system, controlling to form a proper temperature, dissolving bis(trichloromethyl)carbonate in a certain amount of the organic solvent to obtain a mixture, slowly dropwise adding the mixture into the raw material system for reaction, and after the reaction is finished, carrying out column chromatography isolation, so as to obtain 2-chloroquinoline. The preparation method is simple, the reaction period is short, and a phosphorus-containing reagent and heavy metals are not adopted;and compared with the prior art, the method has the advantages that the environmental pollution is low, the operation is safe, and the cost is low. The method is applied to the environment-friendly chlorination reaction of quinoline N-oxide and is not limited to the preparation of 2-chloroquinoline.
- -
-
Paragraph 0023-0054
(2019/03/08)
-
- C-Bridged Bispyrrolidines and Bispiperidines as New Ligands
-
The preparation of methylene-bridged C2-symmetric nitrogen-heterocycles as a new class of ligands is described, including methylene-bridged pyridines, quinolones, piperidines and pyrrolidines. These methylene-bridged aromatic systems are obtained via a microwave assisted Ziegler-type reaction. The separation of diastereomers and the application of the copper complexes of these ligands for cyclopropanation reactions proves the applicability of these new types of ligands.
- Stumpf, Tim-Daniel J.,Steinbach, Manfred,H?ltke, Magdalene,Heuger, Gerold,Grasemann, Franka,Fr?hlich, Roland,Schindler, Siegfried,G?ttlich, Richard
-
p. 5538 - 5547
(2018/10/25)
-
- Synthesis and anticancer activity evaluation of some new derivatives of 2-(4-benzoyl-1-piperazinyl)-quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline
-
In this study, we designed and synthesized twenty new derivatives of 2-(4-benzoyl-1-piperazinyl)- quinoline and 2-(4-cinnamoyl-1-piperazinyl)-quinoline with potential anticancer activity. The structures of synthesized compounds were confirmed by 1H and 13C NMR spectroscopy and MS spectrometry. The activity of novel compounds was evaluated in the cell viability assay as well as in the wound healing assay. Presented data show that examined substances have anticancer activity in cell culture. Seven compounds which showed a high rate of cell growth inhibition were selected for further studies. Three of them strongly reduced the growth of B16F10 cells. The novel compounds constitute a good base for further studies and optimization of structure for new therapeutically effective anti-cancerous drugs.
- Kubica, Krzysztof P.,Taciak, Przemys?aw P.,Czajkowska, Agnieszka,Stokfisz-Ignasiak, Alicja,Wyrebiak, Rafa?,Podsadni, Piotr,M?ynarczuk-Bia?y, Izabela,Malejczyk, Jacek,Mazurek, Aleksander P.
-
p. 891 - 901
(2018/09/25)
-
- Preparation method of non-transition metal-catalyzed 2-halogenated pyridine compound
-
The invention provides a preparation method of a non-transition metal-catalyzed 2-halogenated pyridine compound. The 2-halogenated pyridine compound is an important component of many medicines and bioactive molecules and has important application in the fields of organic synthesis, medicinal chemistry and the like and wide market prospects. The invention relates to the preparation method of the non-transition metal-catalyzed 2-halogenated pyridine compound. According to the method, pyridine-2-carboxylic acid, derivatives of the pyridine-2-carboxylic acid, NaF, KF, CsF, TBAF, NaCl, KCl, CsCl, TBAC, NCS, NaBr, KBr, CsBr, Br2, TBAB, NBS, NaI, KI, CsI, I2 and NIS are used as raw materials, and under the presence of base and an accelerant and mild conditions, the 2-halogenated pyridine compoundis synthesized. The method has the advantages that the steps are simple, the raw materials are easy to obtain, the reaction conditions are mild and the like; the method has great use value and socialand economic benefits.
- -
-
Paragraph 0037-0039
(2018/10/11)
-
- Photoreductive Removal of O-Benzyl Groups from Oxyarene N-Heterocycles Assisted by O-Pyridine-pyridone Tautomerism
-
Facile photoreductive protocols have been developed to remove benzyl O-protective groups from oxyarene N-heterocycles at positions capable for 2-/4-O-pyridine-2-/4-pyridone tautomerism. Blue light irradiation, a [Ru] or [Ir] photocatalyst, and ascorbic acid in a water-acetonitrile solution debenzylates a variety of aryl N-heterocycles cleanly and selectively. Ascorbic acid has two functions in the reaction. On the one hand, it protonates the N-heterocycles that reduces their reduction potentials notably and on the other hand it acts as a sacrificial reductant. Reduction potentials and free energy barriers calculated at the CPCM-B3LYP/6-31+G? level can predict the reactivities of the studied substrates.
- Todorov, Aleksandar R.,Wirtanen, Tom,Helaja, Juho
-
p. 13756 - 13767
(2017/12/26)
-
- Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides
-
This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.
- Malapit, Christian A.,Ichiishi, Naoko,Sanford, Melanie S.
-
supporting information
p. 4142 - 4145
(2017/08/15)
-
- N, N-disubstituted benzo-nitrogen heterocycles-2-amine compound and use thereof
-
The invention mainly relates to an N,N-double substituted benzoazacyclo-2-amide compound and an application thereof. The N,N-double substituted benzoazacyclo-2-amide compound is a compound shown as formula I or a salt formed by a medical acid or alkali. The compound provided by the invention has strong inhibition activity on RhoA protease which is tightly related with cardiovascular and cerebrovascular diseases. The compound provided by the invention is hopeful to be developed into a RhoA protease small-molecule inhibitor type cardiovascular and cerebrovascular disease treatment medicine.
- -
-
Paragraph 0082; 0084-0087
(2016/10/09)
-
- Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN
-
A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.
- Qiao, Kai,Wan, Li,Sun, Xiaoning,Zhang, Kai,Zhu, Ning,Li, Xin,Guo, Kai
-
p. 1606 - 1611
(2016/04/05)
-
- Development of a facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines
-
A facile and inexpensive route for the preparation of α-halobenzopyridines from α-unsubstituted benzopyridines via N-methylbenzopyridin-α-ones was developed. α-Unsubstituted benzopyridines were converted easily into the corresponding N-methylbenzopyridin-α-ones, which were halogenated using PPh3-TCICA or PPh3-DBICA without using solvent to give α-halobenzopyridines.
- Sugimoto, Osamu,Iwasaki, Hyuma,Tanji, Ken-Ichi
-
p. 1445 - 1454
(2015/07/15)
-
- Development of second-generation small-molecule RhoA inhibitors with enhanced water solubility, tissue potency, and significant in vivo efficacy
-
RhoA, a member of the Rho GTPases, is involved in a variety of cellular functions and could be a suitable therapeutic target for the treatment of cardiovascular diseases. However, few small-molecule RhoA inhibitors have been reported. Based on our previously reported lead compounds, 32 new 2-substituted quinoline (or quinoxaline) derivatives were synthesized and tested in biological assays. Six compounds showed high RhoA inhibitory activities, with IC50 values of 1.17-1.84 μM. Among these, (E)-3-(3-(ethyl(quinolin-2-yl)amino)phenyl)acrylic acid (26b) and (E)-3-(3-(butyl(quinolin-2-yl)amino)phenyl)acrylic acid (26d) demonstrated noticeable vasorelaxation effects against phenylephrine-induced contraction in thoracic aorta artery rings, and compound 26b had good water solubility and showed significant in vivo efficacy, which was similar to that of 5-(1,4-diazepane-1-sulfonyl)isoquinoline (fasudil) in a subarachnoid hemorrhage-cardiovascular model. To the best of our knowledge, compound 26b is the first example of a small-molecule RhoA inhibitor with potent in vivo efficacy, which could serve as a good lead for designing cardiovascular agents.
- Ma, Sheng,Deng, Jing,Li, Baoli,Li, Xiujiang,Yan, Zhaowei,Zhu, Jin,Chen, Gang,Wang, Zhong,Jiang, Hualiang,Miao, Liyan,Li, Jian
-
p. 193 - 206
(2015/03/13)
-
- A practical and mild chlorination of fused heterocyclic N-oxides
-
Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated.
- Wang, Dong,Jia, Hailing,Wang, Wuchang,Wang, Zhe
-
supporting information
p. 7130 - 7132
(2015/02/02)
-
- Glycinatocopper(II) complex as an efficient heterogeneous catalyst for aromatic Finkelstein reaction of aryl and heteroaryl bromides to chlorides
-
Glycinatocopper(II) complex 1, readily synthesized from copper chloride and glycine was characterized by various techniques including FTIR, XRD, TGA and SEM analysis. The as-synthesized copper complex was found to be a simple and efficient catalyst for the synthesis of aryl and heteroaryl chlorides via aromatic Finkelstein reaction of aryl and heteroaryl bromides in high to excellent yields. The developed glycinatocopper(II) catalyst could easily be recovered from the reaction mixture and reused successfully for several runs without any loss in catalytic efficiency. The developed methodology represents the first example of the use of heterogeneous catalyst for the synthesis of aryl and heteroaryl chlorides via aromatic Finkelstein reaction.
- Verma, Sanny,Saran, Sandeep,Jain, Suman L.
-
p. 178 - 183
(2014/02/14)
-
- Phosphonium chloride as a non-volatile chlorinating reagent: Preparation and reaction in no solvent or ionic liquid
-
Reaction of triphenylphosphine with trichloroisocyanuric acid in no solvent or an ionic liquid gave the corresponding phosphonium chloride, which can be used as a cheap and safe chlorinating reagent. Conversion of hydroxyheterocycles to chloroheterocycles, carboxylic acids to carboxylic acid chlorides, and primary amides to nitriles were accomplished by using the phosphonium chloride in excellent to good yields.
- Sugimoto, Osamu,Harada, Yukihiro,Tanji, Ken-Ichi
-
p. 1583 - 1590
(2013/08/15)
-
- Copper-catalyzed conversion of aryl and heteroaryl bromides into the corresponding chlorides
-
An efficient method for the synthesis of aryl and heteroaryl chlorides is described. The reactions of aryl and heteroaryl bromides with tetramethylammonium chloride proceeded smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding chlorides in satisfactory to excellent yields.
- Feng, Xiujuan,Qu, Yiping,Han, Yanlei,Yu, Xiaoqiang,Bao, Ming,Yamamoto, Yoshinori
-
supporting information
p. 9468 - 9470
(2012/10/29)
-
- Cl3CCN/PPh3 and CBr4/PPh3: Two efficient reagent systems for the preparation of N-heteroaromatic halides
-
Cl3CCN/PPh3 and CBr4/PPh3 are two highly reactive reagent systems for the conversion of N-heteroaromatic hydroxy compounds into N-heteroaromatic chlorides or bromides in moderate to excellent yields under mild and acid-free conditions.
- Kijrungphaiboon, Woranun,Chantarasriwong, Oraphin,Chavasiri, Wainthorn
-
scheme or table
p. 674 - 677
(2012/02/15)
-
- Design and synthesis of small molecule RhoA inhibitors: A new promising therapy for cardiovascular diseases?
-
RhoA is a member of Rho GTPases, a subgroup of the Ras superfamily of small GTP-binding proteins. RhoA, as an important regulator of diverse cellular signaling pathways, plays significant roles in cytoskeletal organization, transcription, and cell-cycle progression. The RhoA/ROCK inhibitors have emerged as a new promising treatment for cardiovascular diseases. However, to date, RhoA inhibitors are macromolecules, and to our knowledge, small molecular-based inhibitors have not been reported. In this study, a series of first-in-class small molecular RhoA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. Virtual screening of ~200,000 compounds, followed by SPR-based binding affinity assays resulted in three compounds with binding affinities to RhoA at the micromolar level (compounds 1-3). Compound 1 was selected for further structure modifications in considering binding activity and synthesis ease. Fourty-one new compounds (1, 12a-v, 13a-h, and 14a-j) were designed and synthesized accordingly. It was found that eight (12a, 12j, 14a, 14b, 14d, 14e, 14 g, and 14h) showed high RhoA inhibition activities with IC50 values of 1.24 to 3.00 μM. A pharmacological assay indicated that two compounds (14g and 14 h) demonstrated noticeable vasorelaxation effects against PE-induced contraction in thoracic aorta artery rings and served as good leads for developing more potent cardiovascular agents.
- Deng, Jing,Feng, Enguang,Ma, Sheng,Zhang, Yan,Liu, Xiaofeng,Li, Honglin,Huang, Huang,Zhu, Jin,Zhu, Weiliang,Shen, Xu,Miao, Liyan,Liu, Hong,Jiang, Hualiang,Li, Jian
-
experimental part
p. 4508 - 4522
(2011/09/14)
-
- Cu(I)-mediated deoxygenation of N-oxides to amines
-
A mild and highly efficient deoxygenation of variety of N-oxides using an inexpensive CuX, or a CuX-Zn or CuX-Al couple is described.
- Singh, Sunil Kumar,Srinivasa Reddy,Mangle, Mangesh,Ravi Ganesh
-
p. 126 - 130
(2007/10/03)
-
- From haloquinolines and halopyridines to quinoline- and pyridinesulfonyl chlorides and sulfonamides
-
The action of sodium methanethiolate (in boiling DMF) towards haloazines (i.e. chloro- or bromo-pyridines and quinolines) (1) (with halogen substituent in non-aza-activated position) causes sequentially halogen ipso-substitution to methylthioazines (2) and then S-demethylation to azinethiolates (3A), which were: i) subjected to S-methylation, ii) oxidized to diazinyl disulfides (4) and iii) oxidatively chlorinated to azinesulfonyl chlorides (5). α- and γ-pyridine- and quinolinesulfonyl chlorides (5a, 5c, 5d and 5f) were prepared by oxidative chlorination of respective disulfides (4) performed in conc. hydrochloric acid and characterized by 1H and 13C NMR spectra. All azinesulfonyl chlorides (5) were effectively converted to corresponding azinesulfonamides (6).
- Maslankiewicz, Andrzej,Marciniec, Krzysztof,Pawlowski, Maciej,Zajdel, Pawel
-
p. 1975 - 1990
(2008/09/16)
-
- Solvent-free reaction using phosphonium salts: Chlorination of hydroxyheteroaromatics and dehydration of primary amides
-
Solvent-free chlorination of heteroaromatics using the phosphonium salt, prepared by reaction of triphenylphosphine with N-chlorosuccinimide, was accomplished by microwave-irradiation or heating to give the corresponding chloroheteroaromatics. Similarly, primary amides was converted into nitriles by this method.{A figure is presented}.
- Takahashi, Tatsuya,Sugimoto, Osamu,Koshio, Jiro,Tanji, Ken-ichi
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p. 1973 - 1979
(2007/10/03)
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- An improved method for chlorination of nitrogen-containing π-deficient heteroaromatics using triphenylphosphine and trichloroisocyanuric acid
-
Phosphorus compound prepared by reaction of triphenylphosphine with trichloroisocyanuric acid was found to be applied to chlorination of nitrogen-containing π-deficient heteroaromatics. As self-decomposition of the chlorinating reagent hardly proceeds, the reagent is more useful than phosphorus compound prepared by triphenylphosphine and N-chlorosuccinimide.
- Sugimoto, Osamu,Tanji, Ken-ichi
-
p. 181 - 185
(2007/10/03)
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- Synthesis of n-chloroquinolines and n-ethynylquinolines (n=2, 4, 8): Homo and heterocoupling reactions
-
The n-(ethynyl)quinolines were satisfactorily prepared by heterocoupling reaction between the appropriate n-chloroquinoline and 2-methyl-3-butyn-2-ol, catalyzed by palladium, followed by treatment with a catalytic amount of powdered sodium hydroxide in toluene. The n-(ethynyl)quinolines were transformed in the corresponding conjugate 1,4-bis[n′-(quinolyl)]buta-1,3-diynes by oxidative dimerization, catalyzed by cuprous chloride, with excellent yields. Moreover, the heterocoupling between n′-haloquinoline and n′-(ethynyl)quinoline (n′, 2′ or 3′), catalyzed by palladium, gives 2′,2′-bis(quinoline) or 1,2-di(3′-quinolyl) ethyne, respectively. The same coupling reaction with zerovalent nickel complexes, gives a mixture of 1,2,4- and 1,3,5-tri(n′-quinolyl)benzene.
- Rodríguez, J. Gonzalo,De Los Rios, Cristobal,Lafuente, Antonio
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p. 9042 - 9051
(2007/10/03)
-
- Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides
-
Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles led to the formation of the corresponding picolinamides in good yields. A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline carboxylic acid. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.
- Kiselyov, Alexander S.
-
p. 2279 - 2282
(2007/10/03)
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- Microwave-assisted dehydration and chlorination using phosphonium salt
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Microwave-assisted reaction using phosphonium salt for dehydration of primary amides and chlorination of hydroxyheteroaromatics was carried out. Copyright Taylor & Francis, Inc.
- Tanji, Ken-Ichi,Koshio, Jiro,Sugimoto, Osamu
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p. 1983 - 1987
(2007/10/03)
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- Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent
-
2-Vinyl- or heteroaryl-substituted anilines were reacted with diphosgene in acetonitrile solution via a reactive imidoyl moiety to afford the corresponding 2-chloroquinolines. Facile syntheses of nine 2-chloroquinoline derivatives from several anilines and their postulate mechanism is described. The postulate mechanism of 2-chloroquinoline formation via imidoyl moiety as a good leaving group shows that the reaction consists of the following three steps: (1) generation of phenylisocyanate, (2) quinoline ring formation, and (3) chlorination on C2 position of quinoline.
- Lee, Byoung Se,Lee, Jae Hak,Chi, Dae Yoon
-
p. 7884 - 7886
(2007/10/03)
-
- Application of phosphonium salts to the reactions of various kinds of amides
-
The phosphonium salts 1 and 2 prepared from triphenylphosphine and N-halogenosuccinimide proved to be applicable to the conversion of amide compounds. Especially, halogenation of electron-deficient heteroaromatic alcohols with these reagents seems to be a convenient method compared to the halogenation with phosphorus oxyhalides.
- Sugimoto, Osamu,Mori, Miho,Moriya, Keisuke,Tanji, Ken-Ichi
-
p. 1112 - 1118
(2007/10/03)
-
- Indium-mediated deoxygenation of amine-N-oxides in aqueous media
-
Several aromatic and aliphatic amine-N-oxides were deoxygenated to the corresponding amines in good to quantitative yield using indium metal in neutral aqueous media. Other functional groups such as alkenes, halides, esters, ethers, nitriles, amides and sulfones are unaffected under the present reaction conditions. (C) 2000 Elsevier Science Ltd.
- Yadav,Subba Reddy,Reddy, M. Muralidhar
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p. 2663 - 2665
(2007/10/03)
-
- A facile halogenation of some hydroxyheterocycles using triphenylphosphine and N-halosuccinimide
-
Some hydroxyheterocycles were halogenated to give the corresponding haloheterocycles using triphenylphosphine and N-halosuccinimide. In comparison with the usual method using phosphorus oxyhalide, the haloheterocycles were easily isolated.
- Sugimoto, Osamu,Mori, Miho,Tanji, Ken-ichi
-
p. 7477 - 7478
(2007/10/03)
-
- A novel reaction of benzoyl chloride adduct of aromatic N-oxide with carbonitrile via a carbene intermediate
-
A carbene intermediate is proposed as a reactive species in the base-induced reaction of benzoyl chloride adducts of pyridine and quinoline N-oxides with carbonitriles to give 2-pyridyl- and 2-quinolyl diacylamine as main products.
- Tagawa, Yoshinobu,Tanaka, Jun'ichi,Hama, Kazuya,Goto, Yoshinobu,Hamana, Masatomo
-
-
- Preparation of substituted 2-chloropyridines
-
A process for the preparation of a substituted 2-chloropyridine derivatives of the formula STR1 in which R1, R2, R3 and R4 represent hydrogen or various other radicals, which comprises reacting a pyridine-1-oxide of the formula STR2 with an aromatic carbonyl chloride in the presence of an inert organic solvent and in the presence of an acid acceptor at a temperature between about -20° C. and 200° C.
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-
-
- Process for the preparation of substituted 2-chloropyridines
-
A new process has been found for the preparation of substituted 2-chloropyridine derivatives of the formula (I) STR1 wherein R1 to R4 have the meanings as defined in the description. The new process is characterized in that pyridine 1-oxides of the formula II STR2 are reacted with a chlorine-containing phosphoric acid derivative from the series of the chlorophosphoric esters and chlorophosphoramides in the presence of an inert organic solvent and in the presence of an acid acceptor at temperatures between -20° C. and 200° C., and the resulting product is separated further, if appropriate. Compound (I) is known as an intermediate product for medicaments (cf.DE-A 2,812,585) or for insecticidel nitromethylene derivatives (cf. EP-A 163,855).
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-
- SYNTHESIS OF HETEROARYLQUINOLINES BY THE PHOTOLYSIS OF 2-, 3-, AND 4-IODOQUINOLINES
-
Photoreaction of 2-, 3-, and 4-iodoquinolines with five membered heterocycles (i.e. 1-methylpyrrole, pyrrole, furan and thiophene) afforded the corresponding n-(2-heteroaryl)quinolines (n=2, 3, 4) in appreciable yields.
- Ohkura, Kazue,Seki, Koh-ichi,Terashima, Masanao,Kanaoka, Yuichi
-
p. 957 - 962
(2007/10/02)
-
- SELECTIVE REDUCTION OF THE N-O BOND IN HETEROAROMATIC N-OXIDES BY TiCl4/SnCl2.
-
Heteroaromatic N-oxides bearing various functionalities are readily and selectively converted under mild conditions into the corresponding bases using TiCl4/SnCl2.
- Balicki, Roman,Kaczmarek, Lukasz,Malinowski, Marek
-
p. 897 - 900
(2007/10/02)
-
- PHOTODECARBOXYLATIVE CHLORINATION OF CARBOXYLIC ACIDS VIA THEIR BENZOPHENONE OXIME ESTERS
-
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.
- Hasebe, Masato,Tsuchiya, Takashi
-
p. 6287 - 6290
(2007/10/02)
-
- Titanium(0) Reagents; 2. A Selective and Efficient Deoxygenation of Halogen Containing Heteroaromatic N-Oxides
-
Following successful reductions of unfunctionalized heteroaromatic N-oxides by titanium(0), we applied this method to halogenated aromatic N-oxides to give the deoxygenated halogeno derivatives in 90-95percent yield.
- Malinowski, Marek,Kaczmarek, Lukasz
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p. 1013 - 1015
(2007/10/02)
-
- Nucleophile and Aryl Radical Reactivity in SRN1 Aromatic Nucleophilic Substitution Reactions. Absolute and Relative Electrochemical Determination
-
Three electrochemical methods are used to obtain the rate of the Ar.+Nu- reaction.In the direct cyclic voltammetric method, the data are derived from the decrease of the substrate peak current upon addition of the nucleophile while in the relative method they are obtained from the peak heights of the two substitution products observed upon repetitive cycling of the substrate solution in the presence of two nucleophiles.In the redox catalysis method , the reduction of the substrate is catalyzed by an exogeneous reversible couple and the data are derived from the decrease of the catalytic current upon addition of the nucleophile.All three methods were combined to determine the reactivities of a series 26 aryl radical-nucleophile couples.In most cases, the rate constant is close to the diffusion limit.The exceptions concern the 2-quinolyl and 2-pyridyl radicals.The results are discussed in terms of energy difference between the ?* and ?* orbitals in the driving force of the reaction as related to characteristic standard potentials and bond energies.
- Amatore, Christian,Oturan, Mehmet A.,Pinson, Jean,Saveant, Jean-Michel,Thiebault, Andre
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p. 3451 - 3459
(2007/10/02)
-