- A mild and simple regioselective iodination of activated aromatics with iodine and catalytic ceric ammonium nitrate
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Molecular iodine in the presence of a catalytic amount of CAN has been utilized efficiently for regioselective iodination of activated aromatic compounds under mild reaction conditions.
- Das, Biswanath,Krishnaiah, Maddeboina,Venkateswarlu, Katta,Reddy, V. Saidi
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- Synthesis of 8-azaprotosappanin A derivatives via intramolecular palladium-catalyzed ortho C-H activation/C-C cyclization and their antibacterial activity
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A novel synthetic protocol for the construction of eight-membered heterocycles by intramolecular palladium-catalyzed ortho C-H activation/C-C cyclization was proposed. With protosappanin A as the lead compound, 25 derivatives of 8-azaprotosappanin A were prepared in good yields by this protocol. Besides, a plausible reaction mechanism of the intramolecular cyclization was proposed. This strategy could be widely used in the synthesis of some natural products and drugs with large heterocycles due to the fast reaction rate and the mild conditions. In vitro antimicrobial activities of the synthesized compounds were assessed against the strains of Gram-positive bacteria and linezolid and ciprofloxacin were selected as the standard drugs. Some of the synthesized compounds were found to have excellent antibacterial activities.
- Zhou, Xuan,Fu, Wanyong,Jiang, Hongshuo,Wang, Chenglong,Ju, Chao,Chu, Wenyi,Sun, Zhizhong
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Read Online
- Synthesis of 1,4-benzoxazepine derivatives via a novel domino aziridine ring-opening and isocyanide-insertion reaction
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A novel and efficient domino process has been developed for the synthesis of 1,4-benzoxazepine derivatives from a range of readily accessible N-tosylaziridines, 2-iodophenols and isocyanides. This process involves the aziridine ring-opening reaction with 2-iodophenol, followed by a palladium-catalyzed isocyanide-insertion reaction. This regioselective and high-yielding transformation could be extended to its application for the synthesis of natural products and biologically interesting heterocycles. Copyright
- Ji, Fei,Lv, Mei-Fang,Yi, Wen-Bin,Cai, Chun
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Read Online
- Synthesis and antimicrobial activity of δ-viniferin analogues and isosteres
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The natural stilbenoid dehydro-δ-viniferin, containing a benzofuran core, has been recently identified as a promising antimicrobial agent. To define the structural elements relevant to its activity, we modified the styryl moiety, appended at C5 of the ben
- Catinella, Giorgia,Dallavalle, Sabrina,Krogfelt, Karen Angeliki,Mattio, Luce Micaela,Musso, Loana,Pedersen, Kasandra Juliet,Pinna, Cecilia,Pinto, Andrea
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supporting information
(2021/12/24)
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- Palladium-Catalyzed Chemoselective Oxidative Addition of Allyloxy-Tethered Aryl Iodides: Synthesis of Medium-Sized Rings and Mechanistic Studies
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This Letter describes a Pd-catalyzed Tsuji-Trost-type/Heck reaction with allyloxy-tethered aryl iodides and aziridines. The strategy provides efficient access to benzannulated medium-sized rings via intermolecular cyclization. The substrate aryl iodide ha
- Liu, Ce,Li, Yuke,Shi, Wei-Yu,Ding, Ya-Nan,Zheng, Nian,Liu, Hong-Chao,Liang, Yong-Min
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supporting information
p. 4311 - 4316
(2021/05/26)
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- Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates
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Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.
- Li, Xue,Chen, Haohua,Xuan, Qingqing,Mai, Shaoyu,Lan, Yu,Song, Qiuling
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supporting information
p. 3518 - 3523
(2021/05/29)
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- Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
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An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
- Satkar, Yuvraj,Yera-Ledesma, Luisa F.,Mali, Narendra,Patil, Dipak,Segura-Quezada, Luis A.,Ramírez-Morales, Perla I.,Solorio-Alvarado, César R.,Navarro-Santos, Pedro
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p. 4149 - 4164
(2019/04/30)
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- Oxyacylation of Iodoalkynes: Gold(I)-Catalyzed Expeditious Access to Benzofurans
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(Acetonitrile)[1,3-bis(2,6-diisopropylphenyl)-imidazole-2-ylidene] gold(I) catalyzes the cycloisomerization of 2-(iodoethynyl)aryl esters to give 3-iodo-2-acyl benzofurans. This catalytic transformation is the result of an unprecedented selective syntheti
- Fernández-Canelas, Paula,Rubio, Eduardo,González, José M.
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supporting information
p. 6566 - 6569
(2019/08/20)
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- One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis
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A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.
- Henry, Martyn C.,McGrory, Rochelle,Faggyas, Réka J.,Mostafa, Mohamed A. B.,Sutherland, Andrew
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p. 4629 - 4639
(2019/05/17)
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- A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones
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A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.
- Wang, Wei-Feng,Peng, Jin-Bao,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 3521 - 3524
(2019/02/14)
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- Hypervalent Iodine(III)-Catalyzed Synthesis of 2-Arylbenzofurans
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An alternative route for the synthesis of 2-arylbenzofurans is described by iodine(III)-catalyzed oxidative cyclization of 2-hydroxystilbenes using 10 mol% (diacetoxyiodo)benzene [PhI(OAc) 2 ] as catalyst in the presence of m -chloroperbenzoic acid. The 2-arylbenzofurans were isolated in good to excellent yields.
- Singh, Fateh V.,Mangaonkar, Saeesh R.
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p. 4940 - 4948
(2018/12/14)
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- Indanol-Based Chiral Organoiodine Catalysts for Enantioselective Hydrative Dearomatization
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Rapid development in the last decade has rendered chiral organoiodine(I/III) catalysis a reliable methodology in asymmetric catalysis. However, due to the severely limited numbers of effective organoiodine catalysts, many reactions still give low to modes
- Hashimoto, Takuya,Shimazaki, Yuto,Omatsu, Yamato,Maruoka, Keiji
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supporting information
p. 7200 - 7204
(2018/06/15)
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- Ultrasonically assisted halogenation of aromatic compounds using isoquinolinium bound hypervalent chromium and tetrabutylammonium halides in PEG-600 solutions under acid free and solvent-free conditions
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Isoquinolinium bound Cr(VI) reagents like isoquinolinium dichromate (IQDC) and isoquinolinium chlorochromate (IQCC) have been successfully accomplished as efficient reagents for oxidative halogenation of aromatic compounds using tetrabutylammonium halide (TBAX) as halogenating agents in aqueous polyethylene glycol (PEG-600) under acid free conditions. Tetrabutylammonium bromide (TBAB) has been used for bromination and tetrabutylammonium iodide (TBAI) for iodination. The halogenation reactions that occurred smoothly in 2 to 7 h under conventional conditions are accelerated magnificently under sonication with few minutes (25 to 70 min) of reaction time and fairly good yields. The reactions occurred at moderate temperature under mild and environmentally safe conditions with simple work up.
- Sambashiva Rao,Ramesh, Kola,Rajanna,Chakrvarthi
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p. 1892 - 1896
(2018/07/10)
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- FIVE-COORDINATE BIS-PHENYLPHENOXY CATALYSTS FOR THE PREPARATION OF ETHYLENE-BASED POLYMERS
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The invention provides a molecular transition metal complex selected from Formula 1, as described herein; an ethylene-based polymer; and a process to form the ethylene-based polymer, said process comprising polymerizing ethylene in the presence of at leas
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Page/Page column 28; 29
(2016/06/28)
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- Total synthesis of protosappanin A and its derivatives via palladium catalyzed ortho C-H activation/C-C cyclization under microwave irradiation
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A total synthesis method for protosappanin A, which is a complex natural product with many biological activities, was developed with 6 linear steps. Dibenzo[b,d]oxepinones as the key intermediates of the synthetic route were prepared by a palladium-catalyzed ortho C-H activation/C-C cyclization under microwave irradiation. 25 derivatives of protosappanin A were obtained.
- Liu, Jiaqi,Zhou, Xuan,Wang, Chenglong,Fu, Wanyong,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 5152 - 5155
(2016/05/02)
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- Isoquinolinium Dichromate and Chlorochromate as Efficient Catalysts for Oxidative Halogenation of Aromatic Compounds under Acid-Free Conditions
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Isoquinolinium dichromate and isoquinolinium chlorochromate were found as efficient catalysts to trigger oxidative bromination and iodination of aromatic hydrocarbons with KBr/KI and KHSO4 under acid-free conditions. Reaction times reduced highly significantly under sonication, followed by corresponding mono bromo derivatives in very good yield with high regioselectivity.
- Rao, A. Sambashiva,Rajanna,Reddy, K. Rajendar,Kulkarni, Subhash
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p. 832 - 837
(2016/02/12)
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- Greener iodination of arenes using sulphated ceria-zirconia catalysts in polyethylene glycol
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An environmentally benign method for the selective monoiodination of diverse aromatic compounds has been developed using reusable sulphated ceria-zirconia under mild conditions. The protocol provides moderate to good yields and selectively introduces iodine at the para/ortho position in monosubstituted arenes. SO42-/Ce0.07Zr 0.93O2 was found to be the best choice for the synthesis of aryl iodides in high yield, presumably due to the maximum number of acid sites (4.23 mmol g-1) among the various compositions of the catalyst system.
- Kahandal, Sandeep S.,Kale, Sandip R.,Gawande, Manoj B.,Zboril, Radek,Varma, Rajender S.,Jayaram, Radha V.
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p. 6267 - 6274
(2014/01/23)
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- 2,2′-biphenols via protecting group-free thermal or microwave-accelerated suzuki-miyaura coupling in water
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User-friendly protocols for the protecting group-free synthesis of 2,2′-biphenols via Suzuki-Miyaura coupling of o-halophenols and o-boronophenol are presented. The reactions proceed in water in the presence of simple additives such as K2CO3, KOH, KF, or TBAF and with commercially available Pd/C as precatalyst. Expensive or laboriously synthesized ligands or other additives are not required. In the case of bromophenols, efficient rate acceleration and short reaction times were accomplished by microwave irradiation.
- Schmidt, Bernd,Riemer, Martin,Karras, Manfred
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p. 8680 - 8688
(2013/09/24)
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- A quantitative structure-reactivity assessment of phenols by investigation of rapid iodination kinetics using hydrodynamic voltammetry: Applicability of the Hammett equation in aqueous medium
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Halogenations of aromatic substrates in aqueous medium are essentially electrophilic substitutions proceeding at rates concomitant with the nature of the substrates and substituent motifs. Kinetics as an investigatory tool for the quantitative assessment of the structure-reactivity correlation in these reactions for a diverse range of substrates has rarely been reported, presumably due to the rapidity of these reactions in aqueous medium. We have used hydrodynamic voltammetry to investigate the rapid kinetics of uncatalyzed iodination of phenol and eight substituted phenols by iodine monochloride at constant pH in aqueous medium. The Arrhenius plots for these reactions yield comprehensive kinetic and thermodynamic data. The quantitative structure-reactivity correlation stemming from the regio- and stereospecificity of the substituent motifs on the substrates has been examined through the Hammett plot, which shows a negative slope of 1.87. The magnitudes of the rate constants, energies of activation, frequency factors, and entropy change obtained for the nine fast reactions reported, reflect the relative ease of the reaction dynamics in quantitative terms thereby ascertaining the relative reactivities of the phenols studied herein.
- Borkar, Vitthal T.,Bonde, Shantaram L.,Dangat, Vijay T.
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p. 693 - 702
(2013/10/21)
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- One-pot synthesis of 2,2′-bisbenzofurans using cuprous chloride as a catalyst
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A variety of novel 5,5′-disubstituted-2,2′-bisbenzofuran derivatives were synthesized by treatment of 4-substituted-2-(2- trimethylsilylethynyl)phenyl tert-butyldimethylsilyl ether analogues with CuCl as a catalyst in 62-82% isolated yields. This novel st
- Pan, Wen-Bin,Chen, Chin-Chau,Wei, Li-Lan,Wei, Li-Mei,Wu, Ming-Jung
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p. 2655 - 2657
(2013/06/05)
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- Gas-Chromatographic identifi cation of products formed in iodination of methyl phenols by retention indices
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Iodination reaction followed by conversion of iodine-substituted methylphenols to the corresponding trifl uoroacetates was suggested for improving the sensitivity of the gas-chromatographic determination of phenol and its methyl-substituted derivatives (al isomers of mono- and diethylphenols, 2,3,5-, 2,3,6-, and 3,4,5-trimethylphenols) in aqueous media. Acylation products of iodo methylphenols (104 compounds) were identifi ed by linear-logarithmic retention indices on a standard nonpolar polydimethylsiloxane stationary phase, and the pattern of their variation with the number and nature of substituents were characterized. A procedure for identifi cation of methyl-substituted phenols in water in their gas-chromatographic determination with an electron-capture detector was developed. Pleiades Publishing, Ltd., 2012.
- Gruzdev,Kuzivanov,Zenkevich,Kondratenok
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p. 1355 - 1365
(2013/01/15)
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- Efficient iodination of aromatic compounds using potassium ferrate supported on montmorillonite
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Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure.
- Keipour, Hoda,Khalilzadeh, Mohammad A.,Mohtat, Bita,Hosseini, Abolfazl,Zareyee, Daryoush
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experimental part
p. 1427 - 1430
(2012/06/01)
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- Green and efficient method for the iodination of phenols in water
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In this article, green conversion of phenols to the corresponding iodide derivatives is reported. The reactions were conducted in water, using potassium iodide as the source of iodine and potassium ferrate as the oxidizing agent. The selected phenols were successfully iodinated in good to excellent yields in mild and non-toxic reaction conditions. Copyright Taylor & Francis Group, LLC.
- Tajik, Hassan,Dadras, Akbar,Hosseini, Abolfazl
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experimental part
p. 258 - 261
(2011/06/26)
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- Synthesis and antimicrobial evaluation of new benzofuran derivatives
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Thirteen compounds, based on benzofuran skeleton bearing aryl substituents at its C-3 position through methanone linker, were synthesized and screened for their antibacterial and antifungal activities against four bacteria Escherichia coli, Staphylococcus aureus, Methicillin-resistant S. aureus, Bacillus subtilis, and a fungus Candida albicans. Four hydrophobic benzofuran analogs were found to exhibit favorable antibacterial activities (MIC80 = 0.39-3.12 μg/mL), which were better than the control drugs.
- Jiang, Xizhen,Liu, Wenlu,Zhang, Wei,Jiang, Faqin,Gao, Zhe,Zhuang, Hao,Fu, Lei
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experimental part
p. 3526 - 3530
(2011/07/31)
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- A mild and simple iodination of phenols with trichloroisocyanuric acid/I2/wet SiO2 system
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Molecular iodine in the presence of trichloroisocyanuric acid and wet sio2 has been utilized efficiently for iodination of phenols under mild reaction conditions.
- Akhlaghinia, Batool,Rahmani, Marzieh
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experimental part
p. 3 - 6
(2010/08/19)
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- Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide
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An efficient synthesis of 1-iodoalkynes and iodophenols was easily achieved by employing simple KI and TBHP. The reaction does not involve the use of a metal and base combination. A variety of substituted alkynes and phenols were prepared with good to excellent yield.
- Rajender Reddy,Venkateshwar,Uma Maheswari,Santhosh Kumar
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supporting information; experimental part
p. 2170 - 2173
(2010/06/14)
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- Domino synthesis of 2-arylbenzo[b]furans by copper(II)-catalyzed coupling of o-iodophenols and aryl acetylenes
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A wide range of 2-arylbenzo[b]furans are synthesized through domino intermolecular C(aryl)-C(alkynyl) bond formation followed by intramolecular C(alkynyl)-O bond forming cyclization via copper(II)-catalyzed coupling of o-iodophenols and aryl terminal acetylenes. This method requires neither expensive palladium catalyst nor oxophilic phosphine ligands, can tolerate different functional groups. The methodology is successfully utilized in formal synthesis of β-amyloid aggregation inhibitor 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl) benzofuran.
- Jaseer,Prasad,Sekar, Govindasamy
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supporting information; experimental part
p. 2077 - 2082
(2010/04/29)
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- Domino ring-opening/carboxamidation reactions of N-tosyl aziridines and 2-halophenols/pyridinol: Efficient synthesis of 1,4-benzo- And pyrido-oxazepinones
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"Chemical Equation Presented" A domino process is described for the synthesis of 1,4-benzo- and pyrido-oxazepinones by one-pot sequential ring-opening/carboxamidation reactions of various N-tosylaziridines with a range of 2-halophenols/pyridinol under phase-transfer catalysis.
- Chouhan, Gagan,Alper, Howard
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supporting information; experimental part
p. 192 - 195
(2010/04/02)
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- Ecofriendly iodination of activated aromatics and coumarins using potassium iodide and ammonium peroxodisulfate
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An environmentally benign protocol for the iodination of activated aromatics, such as phenols, anilines, and hydroxycou-marins, using inexpensive commercially available potassium iodide and ammonium peroxodisulfate (1:2.5 molar equivalents per mole of substrate) in aqueous methanol (MeOH-H 2O, 6:1) at room temperature has been developed. The protocol provides for ortho-selective monoiodination as the predominant product without added acid and it is compatible with a number of common oxidizible functional groups, such as formyl, benzylic C-H, aromatic amines and hydroxymethyl. Good to acceptable yields of monoiodinated products in acceptable reaction times and exclusive ortho-iodination for 7-hydroxycoumarins, despite the presence of vinylogous electronrich C3, are some of the key advantageous features of the method. Georg Thieme Verlag Stuttgart.
- Ganguly, Nemai C.,Barik, Sujoy Kumar,Dutta, Sanjoy
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experimental part
p. 1467 - 1472
(2010/09/16)
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- Syntheses and bioactivity of o- or p-trifluoromethylphenyl phosphates
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o- and p-Trifluoromethylphenyl phosphates designed as mechanism-based phosphotyrosine phosphatase inactivators have been prepared. Some of them show herbicidal activities.
- Zhou, Xinming,He, Yantao,Wang, Miao,Ding, Yixiang
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experimental part
p. 651 - 659
(2009/11/30)
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- Regioselective iodination of phenol and analogues using N-iodosuccinimide and p-toluenesulfonic acid
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Mild and highly regioselective monoiodination of phenol and analogues is achieved in high to excellent yields at room temperature with a combination of stoichiometric p-toluenesulfonic acid and N-iodosuccinimide.
- Bovonsombat, Pakorn,Leykajarakul, Juthamard,Khan, Chiraphorn,Pla-on, Kawin,Krause, Michael M.,Khanthapura, Pratheep,Ali, Rameez,Doowa, Niran
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scheme or table
p. 2664 - 2667
(2009/08/09)
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- Methods and systems for preparing fused heterocyclic compounds using copper(I) catalysts
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A copper(I)-catalyzed procedure for the synthesis of benzo[b]heterocycles. This protocol can be used to synthesize a variety of 2-arylbenzo[b]furans and indoles in good to excellent yields. This method can tolerate a variety of functional groups, does not require the use of expensive additives and is palladium-free.
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Page/Page column 17
(2009/01/24)
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- Regioselective iodination of arenes using iodine/NaBO3· 4H2O system in ionic liquid
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A mild, efficient, and simple protocol was developed for iodination of arenes and heterocyclic compounds with molecular iodine catalyzed by sodium perborate in ionic liquid. The methodology offered iodoarenes in good to excellent yields at room temperature. The protocol proved to be highly selective, as a single isomer was formed exclusively in most of the substrates. Copyright Taylor & Francis Group, LLC.
- Bhilare, Sachin V.,Deorukhkar, Amol R.,Darvatkar, Nitin B.,Salunkhe, Manikrao M.
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p. 2881 - 2888
(2008/12/22)
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- A green reagent for the iodination of phenols
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A new reagent (I2/NaNO2) for the iodination of the aromatic ring of phenols has been discovered. The reaction proceeds at room temperature in 1.5-6 hours. In the presence of this reagent, iodinated compounds are regioselectively formed in significant yields from the corresponding substrates. Georg Thieme Verlag Stuttgart.
- Kiran,Konakahara, Takeo,Sakai, Norio
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experimental part
p. 2327 - 2332
(2009/04/04)
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- Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes
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A simple method for the iodination of activated arenes, using molecular iodine and sodium peroxodisulfate as the oxidant, is presented. The reaction is conducted in the presence of catalytic amounts of tetramethylammonium iodide as a phase-transfer catalyst in acetonitrile. For non-polar substances, which are not soluble in pure acetonitrile such as calix[4]arenes bearing long alkyl chains, a modified reaction is introduced. In this case the phase-transfer catalyst is changed to methyltriphenylphosphonium peroxodisulfate. Chloroform as a cosolvent mediates solubility. Furthermore, we show that the slightly basic conditions obtained upon the addition of sodium bicarbonate have a beneficial effect on the yield. Georg Thieme Verlag Stuttgart.
- Barton, Olaf G.,Mattay, Jochen
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p. 110 - 114
(2008/09/20)
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- Iodination of aromatic compounds using potassium iodide and hydrogen peroxide
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A simple, efficient, regioselective, and ecofriendly method for oxyiodination of aromatic compounds is presented. In this method, the electrophilic substitutions of iodine generated in situ from KI as an iodine source and hydrogen peroxide as an oxygen source have been employed without any catalyst/mineral acid for the first time. Copyright Taylor & Francis Group, LLC.
- Reddy, K. Suresh Kumar,Narender,Rohitha,Kulkarni
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experimental part
p. 3894 - 3902
(2009/04/04)
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- Dual aromatase-steroid sulfatase inhibitors
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By introducting the steroid sulfatase inhibitory pharmacophore into aromatase inhibitor 1 (YM511), two series of single agent dual aromatase-sulfatase inhibitors (DASIs) were generated. The best DASIs in'vitro (JEG-3 cells) are 5, (IC50(aromatase) = 0.82 nM; IC 50(sulfatase) = 39 nM), and 14, (IC50(aromatase) = 0.77 nM; IC50(sulfatase) = 590 nM). X-ray crystallography of 5, and docking studies of selected compounds into an aromatase homology model and the steroid sulfatase crystal structure are presented. Both 5 and 14 inhibit aromatase and sulfatase in PMSG pretreated adult female Wistar rats potently 3 h after a single oral 10 mg/kg dose. Almost complete dual inhibition is observed for 5 but the levels were reduced to 85% (aromatase) and 72% (sulfatase) after 24 h. DASI 5 did not inhibit aldosterone synthesis. The development of a potent and selective DASI should allow the therapeutic potential of dual aromatase-sulfatase inhibition in hormone-dependent breast cancer to be assessed.
- Woo, L. W. Lawrence,Bubert, Christian,Sutcliffe, Oliver-B.,Smith, Andrew,Chander, Surinder K.,Mahon, Mary F.,Purohit, Atul,Reed, Michael J.,Potter, Barry V. L.
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p. 3540 - 3560
(2008/02/09)
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- Eco-friendly oxyiodination of aromatic compounds using ammonium iodide and hydrogen peroxide
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A new eco-friendly procedure for the oxyiodination of aromatic compounds with NH4I as an iodine source and H2O2 as an oxidant without any catalyst is presented.
- Narender,Reddy, K. Suresh Kumar,Mohan, K.V.V. Krishna,Kulkarni
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p. 6124 - 6128
(2008/03/12)
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- Pd-catalyzed copper-free carbonylative Sonogashira reaction of aryl iodides with alkynes for the synthesis of alkynyl ketones and flavones by using water as a solvent
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The Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction to synthesize alkynyl ketones from terminal alkynes and aryl iodides was achieved by using water as a solvent. The reaction was carried out at room temperature under balloon pressure of CO with Et3N as a base. The developed method was successfully applied to the synthesis of flavones.
- Liang, Bo,Huang, Mengwei,You, Zejin,Xiong, Zhengchang,Lu, Kui,Fathi, Reza,Chen, Jiahua,Yang, Zhen
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p. 6097 - 6100
(2007/10/03)
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- Synthesis of 2-Arylbenzo[b]furans via Copper(I)-Catalyzed Coupling of o-Iodophenols and Aryl Acetylenes
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(Equation Presented) We report a copper(I)-catalyzed procedure for the synthesis of 2-arylbenzo[b]furans. This protocol can be used to synthesize a variety of 2-arylbenzo[b]furans in good to excellent yields. This method can tolerate a variety of functional groups, does not require the use of expensive additives, and is palladium-free.
- Bates, Craig G.,Saejueng, Pranorm,Murphy, Jaclyn M.,Venkataraman
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p. 4727 - 4729
(2007/10/03)
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- Regioselective oxyiodination of aromatic compounds using potassium iodide and oxone
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A highly efficient, simple, mild and regioselective method for oxyiodination of aromatic compounds is reported. The electrophilic substitution of iodine generated in situ from KI as an iodine source and oxone as an oxidant for the first time.
- Narender,Srinivasu,Kulkarni,Raghavan
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p. 2319 - 2324
(2007/10/03)
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- Iodothyronine Deiodinase Mimics. Deiodination of o,o'-Diiodophenols by Selenium and Tellurium Reagents
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To better understand, and in the extension mimic, the action of the three selenium-containing iodothyronine deiodinases, o,o'-diiodophenols were reacted under acidic conditions with sodium hydrogen telluride, benzenetellurol, sodium hydrogen selenide, or benzeneselenol and under basic conditions with the corresponding deprotonated reagents. Sodium hydrogen telluride was found to selectively remove one iodine from a variety of 4-substituted o,o'-diiodophenols, including a protected form of thyroxine (T4). Thus, it mimics the D1 variety of the iodothyronine deiodinases. Sodium telluride was a more reactive deiodinating agent toward o,o'-diiodophenols, often causing removal of both halogens. Benzenetellurol and sodium benzenetellurolate sometimes showed useful selectivity for monodeiodination. However, the products were often contaminated by small amounts of organotellurium compounds. Sodium hydrogen selenide, sodium selenide, benzeneselenol, and sodium benzeneselenolate were essentially unreactive toward o,o'-diiodophenols. To gain more insight into thyroxine inner-ring deiodination, substituted 2,6-diiodophenyl methyl ethers were treated with some of the chalcogen reagents. Reactivity and selectivity for monodeiodination varied considerably depending on the substituents attached to the aromatic nucleus. In general, it was possible to find reagents that could bring about the selective mono- or dideiodination of these substrates.
- Vasil'ev, Andrei A.,Engman, Lars
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p. 3911 - 3917
(2007/10/03)
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- Iodination of Thallium(I) salts of Phenols
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The iodination of thallium(I) salts of phenols is examined and the results are compared with those of the selective ortho-iodinating reagent thallium(I) acetate-iodine.
- Gambie, Richard C.,Larsen, David S.,Rutledge, Peter S.,Woodgate, Paul D.
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p. 767 - 769
(2007/10/03)
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- A Facile Route to 3a,8a-Dihydrofurobenzofurans.
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Consecutive employment of palladium-catalysis and samarium(II)iodide-induced radical chemistry allows access to analogues of the ABC enol ether tricycle of aflatoxin B1 (1).The Pd-assisted coupling of tributylstannyl ethers of various 2-iodophenols with 2
- Holzapfel, Cedric W.,Williams, D. Bradley G.
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p. 8555 - 8564
(2007/10/02)
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- Electrophilic Aromatic Substitution Reactions: Part I - Kinetics of Iodination of ortho- and para-Substituted Phenols by Iodine Monochloride in Aqueous Methanol
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Iodination of phenol and several p- and o-substituted phenols by iodine monochloride in aqueous methanol (30percent v/v), shows first order dependence each in and and is overall second order.The effects of added perchloric acid and sodiu
- Shashidhar, G. V. S.,Satyanarayana, N.,Sundaram, E. V.
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p. 289 - 291
(2007/10/02)
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- IODINATION OF PHENOLS USING CHLORAMINE T AND SODIUM IODIDE
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A convenient procedure for the iodination of many substituted phenols uses chloramine T and sodium iodide in DMF, DMSO, or acetonitrile.
- Kometani, Tadashi,Watt, David S.,Ji, Tae
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p. 2043 - 2046
(2007/10/02)
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- Kinetics and Mechanism of Iodination of Phenol and Substituted Phenols by Iodine Monochloride in Aqueous Acetic Acid
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In the title reactions the order with respect to ICl is unity and with respect to the substrate it is fractional in the concentration range studied.The effect of varying is negligible at lower acid (HClO) concentrations but at higher (> 0.01 M) there is unit dependence on .From the double reciprocal plot of 1/k1 versus 1/ the decomposition constants have been evaluated.Using these a linear ρ+ - ?+ plot is obtained indicating C-iodination.A mechanism consistent with the results obtained has been postulated.
- Prasada Rao, M. D.,Padmanabha, J.
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p. 133 - 135
(2007/10/02)
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