- Syntheses of Heterocycle-2,3-Fused Indoline and Azaindoline -Derivatives
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We describe a practical method for synthesizing heterocycle-2,3-fused indoline or azaindoline derivatives through haloetherification and cyclization. We applied this method in syntheses of six- to eight-membered heterocycle-2,3-fused indoline and azaindoline derivatives. These derivatives, which contain sp 3 -hybridized carbons, might be useful as new scaffolds in medicinal chemistry.
- Nishi, Takahide,Mishima, Naoki,Kato, Haruna,Yamada, Koji
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- Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons
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A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).
- Yang, Yi,Gao, Xinyan,Zeng, Xiaojun,Han, Junbin,Xu, Bo
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supporting information
p. 1297 - 1300
(2020/12/23)
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- Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics
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Alkoxyamide has been reported as a catalyst for the activation ofN-bromosuccinimide to perform bromocyclization and bromination of a wide range of substrates in a lipophilic solvent, where adequate suppression of the background reactions was observed. The key feature of the active site is the alkoxy group attached to the sulfonamide moiety, which facilitates the acceptance as well as the delivery of bromonium species from the bromine source to the substrates.
- Mondal, Haripriyo,Sk, Md Raja,Maji, Modhu Sudan
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supporting information
p. 11501 - 11504
(2020/10/12)
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- Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
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Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
- Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
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p. 3860 - 3865
(2018/04/26)
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- Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol
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Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.
- Tang, Ren-Jin,Milcent, Thierry,Crousse, Benoit
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p. 930 - 938
(2018/01/28)
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- 2-Hydroxyindoline-3-triethylammonium Bromide: A Reagent for Formal C3-Electrophilic Reactions of Indoles
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A novel indole-2,3-epoxide equivalent, 2-hydroxyindoline-3-triethylammonium bromide, was found to be a convenient reagent for formal C3-electrophilic reactions of indoles with various nucleophiles. By taking advantage of the nucleophilic character of the
- Abe, Takumi,Suzuki, Takuro,Anada, Masahiro,Matsunaga, Shigeki,Yamada, Koji
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supporting information
p. 4275 - 4278
(2017/08/23)
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- Synthesis of 2-arylindoles by Suzuki coupling reaction of 3-bromoindoles with hindered benzoboronic acids
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A new synthetic method for 2-arylindoles has been developed, the process through Suzuki coupling reaction of 3-bromoindoles with hindered boronic acid catalyzed by Pd(OAc)2/PCy3, and a series of 2-arylindoles have been synthesized in moderate to high yields.
- Yue, Guizhou,Wu, Yao,Wu, Caimei,Yin, Zhongqiong,Chen, Huabao,Wang, Xianxiang,Zhang, Zuming
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supporting information
p. 666 - 669
(2017/01/25)
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- A quick, mild and efficient bromination using a CFBSA/KBr system
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Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.
- Jiang, Pan-Pan,Yang, Xian-Jin
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p. 90031 - 90034
(2016/10/09)
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- An organoelectro luminescent compounds and organoelectro luminescent device using the same
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The present invention relates to an organic luminescent compound represented by chemical formula 1 and an organic electroluminescent element comprising the same. An organic electroluminescent element using an organic luminescent compound according to the present invention can be driven at a lower voltage than an existing element using a phosphorescent host material and has high power efficiency.COPYRIGHT KIPO 2016
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- A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles
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A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.
- Maddox, Sean M.,Nalbandian, Christopher J.,Smith, Davis E.,Gustafson, Jeffrey L.
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supporting information
p. 1042 - 1045
(2015/03/30)
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- Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin
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Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.
- Yan, Jianwei,Ni, Tianjun,Yan, Fulin
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supporting information
p. 1096 - 1098
(2015/02/19)
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- Total synthesis of carbazomycin G by a thermal ring expansion/self-redox reaction cascade
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The total synthesis of carbazomycin G (7) has been accomplished in six steps and 26% overall yield starting from commercially available materials. As an efficient access to the tricyclic skeleton of carbazomycins A-H, an interesting thermal ring expansion/self-redox reaction cascade of intermediate 11 has been developed in our study. The self-redox reaction of intermediate 10 can be readily accelerated in the presence of triethylamine, and a plausible reaction mechanism for this process has been proposed. Finally, the synthesis of carbazomycin G was completed by the widely applied regioselective methylation reaction. Copyright
- An, Yong,Wang, Yunxia,Hu, Xiangdong
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p. 3715 - 3718
(2014/06/23)
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- Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors
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Sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors are the current focus on the indication for the management of hyperglycemia in diabetes. Here, a novel series of C-linked indolylxyloside-based inhibitors of SGLT2 has been discovered. Structure-activity relationship studies revealed that substituents at the 7-position of the indole moiety and a p-cyclopropylphenyl group in the distal position were necessary for optimum inhibitory activity. The pharmacokinetic study demonstrates that the most potent compound 1i is metabolically stable with a low clearance in rats. In further efficacy study, 1i is found to significantly lower blood glucose levels of streptozotocin (STZ)-induced diabetic rats.
- Yao, Chun-Hsu,Song, Jen-Shin,Chen, Chiung-Tong,Yeh, Teng-Kuang,Hsieh, Tsung-Chih,Wu, Szu-Huei,Huang, Chung-Yu,Huang, Yu-Lin,Wang, Min-Hsien,Liu, Yu-Wei,Tsai, Chi-Hui,Kumar, Chidambaram Ramesh,Lee, Jinq-Chyi
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p. 32 - 38,7
(2020/07/31)
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- THIAZOLE DERIVATIVES AS SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
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The present invention relates to a novel compound with thiazole ring having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney, and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes.
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- Regioselective copper-catalyzed chlorination and bromination of arenes with O2 as the oxidant
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Electron-rich aromatic C-H bonds undergo regioselective chlorination and bromination in the presence of CuX2, LiX (X = Cl, Br) and molecular oxygen. Preliminary mechanistic insights suggest that the bromination and chlorination reactions proceed by different pathways.
- Yang, Lujuan,Lu, Zhan,Stahl, Shannon S.
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supporting information; experimental part
p. 6460 - 6462
(2010/03/04)
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- 1-SUBSTITUTED-3- BETA-D-GLUCOPYRANOSYLATED NITROGENOUS HETERO- CYCLIC COMPOUNDS AND MEDICINES CONTAINING THE SAME
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A compound having an SGLT1 and/or SGLT2 inhibitory activity which is usable as an agent for the prevention or treatment of diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications, obesity, etc. It is a 1-substituted-3-(β-D
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Page/Page column 14
(2008/06/13)
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- α1b-adrenergic receptor antagonists
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There are provided compounds represented by the general formula (I): [wherein Ar is indole etc., R1is hydrogen etc., B is bond, or B—N—R1forms a ring structure and is piperidine etc., n is 0, 1, etc., A is trimethylene, butylene, etc., Q is piperidine, isoindoline, etc.], or pharmacologically acceptable acid addition salts thereof, and α1B adrenoceptor antagonists composed of these substances. The invented compounds are antagonists having high affinity for α1B adrenoceptor and are useful as pharmaceutical agents for use in prophylaxis/therapy of diseases (e.g., hypertension) in which α1B adrenoceptor is involved or as pharmacological tools for elucidation of physiological activities mediated by α1B adrenoceptor.
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Page/Page column 76
(2010/11/30)
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- Electrophilic fluorination in the synthesis of new fluoroindoles
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Fluorination of trialkylstannylindoles with caesium fluoroxysulfate on Selectfluor(TM) was investigated for the synthesis of inter-alia 2- and 3- fluoroindoles. Caesium fluoroxysulfate gave good yields of these potentially useful intermediates. Selectfluo
- Hodson, Harold F.,Madge, David J.,Slawin, Alexandra N. Z.,Widdowson, David A.,Williams, David J.
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p. 1899 - 1906
(2007/10/02)
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- Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles. Approaches to Ergot Alkaloids
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An efficient synthesis of 4-bromo-1-tosylindole (10) based on the Pd(II)-catalyzed cyclization of an o-ethenylaniline p-toluenesulfonamide has been developed.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted 10 to a number of 4-substituted 1-tosylindoles.Selective electrophilic substitutions at the 3-position of 10 provided access to the 3-(chloromercurio)- (18) and 3-iodo-1-tosylindoles (22).Transmetalation to palladium and allyl chloride insertion converted 18 to 3-allyl-4-bromo-1-tosylindole (20) which could be cyclized to the benzindoline 21.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted the 3-iodo compound 22 to a number of 4-bromo-3-substituted 1-tosylindoles including 24, a potential precursor to optically active tryptophans.
- Harrington, Peter J.,Hegedus, Louis S.
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p. 2658 - 2662
(2007/10/02)
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