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The X-ray structure of 5-chlorosalicylaldehyde
5-Chlorosalicylaldehyde [monoclinic, a = 3.800(2), b = 5.595(4), c = 15.174(11) ?, β = 93.221(17), space group P21] exhibits an unusual crystal structure with both intramolecular and intermolecular OH to CH=O hydrogen bonding, the latter leading to chains of molecules aligned along the b axis. A survey of previous substituted salicylaldehyde structures shows three main hydrogen bonding patterns: intramolecular only (14), intramolecular and intermolecular dimeric (5), and intramolecular and intermolecular polymeric (3).
Aitken, R. Alan,Gidlow, Anna L. G.,Ramsewak, Russel S.,Slawin, Alexandra M. Z.
p. 65 - 69
(2013)
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Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles
A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.
Huang, You,Li, Xiaohu
supporting information
p. 9934 - 9937
(2021/10/12)

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)
N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.
Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information

(2021/01/04)

Driving the Emission Towards Blue by Controlling the HOMO-LUMO Energy Gap in BF2-Functionalized 2-(Imidazo[1,5-a]pyridin-3-yl)phenols
Several boron compounds with 2-(imidazo[1,5-a]pyridin-3-yl)phenols, differentiated by the nature of the substituent (R) in the para position of the hydroxy group, have been synthesized and thoroughly characterized both in solution (1H, 13C, 11B, 19F NMR) and in the solid state (X-ray). All derivatives displayed attractive photophysical properties like very high Stokes shift, high fluorescence quantum yields and a good photostability in solution. Time-Dependent Density Functional Theory (TD-DFT) calculations allowed to define the main electronic transitions as intra ligand transitions (1ILT), which was corroborated by the Natural Transition Orbitals (NTOs) shapes. The HOMO-LUMO energy gap was correlated to the electronic properties of the substituent R on the phenolic ring, as quantified by its σp Hammett constant.
Colombo, Gioele,Attilio Ardizzoia,Furrer, Julien,Therrien, Bruno,Brenna, Stefano
supporting information
p. 12380 - 12387
(2021/07/16)

Copper(II) N, N, O-Chelating Complexes as Potential Anticancer Agents
Three novel dinuclear Cu(II) complexes based on a N,N,O-chelating salphen-like ligand scaffold and bearing varying aromatic substituents (-H, -Cl, and -Br) have been synthesized and characterized. The experimental and computational data obtained suggest that all three complexes exist in the dimeric form in the solid state and adopt the same conformation. The mass spectrometry and electron paramagnetic resonance results indicate that the dimeric structure coexists with the monomeric form in solution upon solvent (dimethyl sulfoxide and water) coordination. The three synthesized Cu(II) complexes exhibit high potentiality as ROS generators, with the Cu(II)/Cu(I) redox potential inside the biological redox window, and thus being able to biologically undergo Cu(II)/Cu(I) redox cycling. The formation of ROS is one of the most promising reported cell death mechanisms for metal complexes to offer an inherent selectivity to cancer cells. In vitro cytotoxic studies in two different cancer cell lines (HeLa and MCF7) and in a normal fibroblast cell line show promising selective cytotoxicity for cancer cells (IC50 about 25 μM in HeLa cells, which is in the range of cisplatin and improved with respect to carboplatin), hence placing this N,N,O-chelating salphen-like metallic core as a promising scaffold to be explored in the design of future tailor-made Cu(II) cytotoxic compounds.
Pe?a, Quim,Sciortino, Giuseppe,Maréchal, Jean-Didier,Bertaina, Sylvain,Simaan, A. Jalila,Lorenzo, Julia,Capdevila, Mercè,Bayón, Pau,Iranzo, Olga,Palacios, òscar
p. 2939 - 2952
(2021/03/08)

Complete chemical shift assignment and molecular modeling studies of two chromene derivatives as potential leads for new anticancer drugs
The compounds 7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (5) and 5-[-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione (7), were synthesized from dimedone and barbituric acid and had their three-dimensional structures and precise chemical shifts assignments obtained by Nuclear Magnetic Resonance (NMR) from 1H, 13C, APT, COSY, HSQC, and HMBC spectra. Additional HOMO-LUMO DFT calculations corroborated the NMR results and pointed to the most stable stereoisomers of each compound. Besides, further docking and molecular dynamic studies suggest that the stereoisomers (9S)-7-chloro-9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one, and 5-[(5S)-7-chloro-2,4-dioxo-1H, 2H, 3H, 4H, 5H-chromeno[2,3-d]pyrimidin-5-yl)]-1,3-diazinane-2,4,6-trione of these compounds may act as DNA intercalators and qualify as potential leads for the development of new anticancer drugs. Communicated by Ramaswamy H. Sarma.
Almeida, Joyce Sobreiro Francisco Diz de,Ferreira Neto, Denise Cristian,Figueroa-Villar, José Daniel,Fran?a, Tanos Celmar Costa,Goncalves, Arlan da Silva,Rubim de Santana, Priscila Ivo
p. 1 - 11
(2020/07/17)

Directed Structural Transformations of Coordination Polymers Supported Single-Site Cu(II) Catalysts to Control the Site Selectivity of C-H Halogenation
A main difficulty in C-H bond functionalization is to undertake the catalyst control accurately where the reaction takes place. In this work, to achieve highly effective and regioselective single-site catalysts, a three-dimensional (3D) rhombus-like framework of {[Mn(Hidbt)DMF]·H2O}n (1) [H3idbt = 5,5′-(1H-imidazole-4,5-diyl)-bis(2H-tetrazole)] containing coordinated DMF molecules was constructed. For the dissolution-recrystallization structural transformation process, attractive structural transformations proceeded from 1 to a new crystalline species formulated as {[Mn3(idbt)2(H2O)2]·3H2O}n (2) with a 3D windowlike architecture, and then the Mn ions in 2 could be exchanged with Cu ions through cation exchange in a single-crystal to single-crystal fashion to produce the Cu-exchanged product {[Mn2Cu(idbt)2(H2O)2]·3H2O}n (2a), which had a windowlike framework like that of 2. Furthermore, 2 and 2a were used as heterogeneous catalysts for the regioselective C-H halogenation of phenols with N-halosuccinimides (NCS and NBS) to produce the site selective single monohalogenated products. It was found that the catalytic activity and site selectivity of 2a were much higher than those of 2, because the unique structural features of 2a with the uniformly dispersed CuII active centers served as a single-site catalyst with a site-isolated and well-defined platform to promote the C-H halogenation reaction in regiocontrol and guide an orientation that favored the para selectivity during the reaction process.
Huang, Chao,Zhu, Kaifang,Zhang, Yingying,Shao, Zhichao,Wang, Dandan,Mi, Liwei,Hou, Hongwei
supporting information
p. 12933 - 12942
(2019/10/11)

Thiocyanate radical mediated dehydration of aldoximes with visible light and air
We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.
Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang
supporting information
p. 9701 - 9704
(2019/08/15)

Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines
A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.
Wang, Chang,Li, Yan,Wu, Yang,Wang, Qijun,Shi, Wangyu,Yuan, Chunhao,Zhou, Leijie,Xiao, Yumei,Guo, Hongchao
supporting information
p. 2880 - 2883
(2018/05/29)

Synthesis, anti-inflammatory evaluation in vivo and docking studies of some new 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin-3(2H)-one derivatives
Seven novel 5-(benzo[b]furan-2-ylmethyl)-6-methyl-pyridazin-3(2H)-one derivatives (6a to 6g) have been synthesized by the condensation of appropriate 3-(benzofuran-2-ylmethylene)-4-oxopentanoic acid and hydrazine hydrate in ethanol. Structures of all compounds were elucidated by elemental analysis, IR, 1H NMR and 13C NMR. These compounds were tested for their anti-inflammatory activity in carrageenan-induced rat paw edema model. In silico molecular docking study has been executed to study the binding interactions of the synthesized compounds with COX-2 protein. Compounds 6a, 6b, 6e and 6g showed a good anti-inflammatory activity at 50 mg/kg compared with the indometacin at 10 mg/kg and the aspirin at 150 mg/kg and good binding affinity with COX-2.
Boukharsa, Youness,Lakhlili, Wiame,El harti, Jaouad,Meddah, Bouchra,Tiendrebeogo, Ramata Yvette,Taoufik, Jamal,El Abbes Faouzi, My,Ibrahimi, Azeddine,Ansar, M'hammed
p. 119 - 127
(2017/10/13)

Cytotoxicity of new pyridazin-3(2H)-one derivatives orchestrating oxidative stress in human triple-negative breast cancer (MDA-MB-468)
Triple-negative breast cancer (TNBC) is a complex and aggressive subtype of breast cancer characterized by high morbidity and mortality. In the absence of targeted therapy, only chemotherapy is available in this case of cancer. The current study investigated the antitumor effect of new pyridazin-3(2H)-one derivatives on the human TNBC cell line, MD-MB-468. The in vitro cytotoxic activities were investigated using the tetrazolium-based MTT assay. Lipid peroxidation, H2O2 content, and the specific activities of antioxidant enzymes were also determined. Two molecules, 6f and 7h, were found to be selectively highly active against tumor cells with IC50 values of 3.12 and 4.9 μM, respectively. Furthermore, cells exposed to 6f showed a significant increase in H2O2 and lipid peroxidation levels, accompanied by a decrease in the enzyme activities of glutathione reductase (GR) and thioredoxin reductase (TrxR). The cytotoxicity of the compound 6f may improve the therapeutic efficacy of the current treatment for TNBC via the inhibition of GR and TrxR activities.
Bouchmaa, Najat,Ben Mrid, Reda,Boukharsa, Youness,Nhiri, Mohamed,Ait Mouse, Hassan,Taoufik, Jamal,Ansar, M'hammed,Zyad, Abdelmajid
(2018/11/02)

Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl
Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.
Rajanna,Rao, A. Sambashiva,Chakravarthi,Reddy, K. Rajendar
p. 167 - 170
(2017/12/26)

NOVEL SUBSTITUTED PYRIDO-PIPERAZINONE DERIVATIVES AS GAMMA SECRETASE MODULATORS
The present invention is concerned with novel substituted pyrido-piperazinone derivatives of Formula (I) wherein R1, R2, R3, R4, R5, L, Z and X have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.
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Paragraph 0786-0787

(2018/11/26)

Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction
Chiral β-amino alcohol ligands were found effective for the copper(ii)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl β-amino alcohols could be conveniently prepared in short steps.
Chen, Wei,Zhou, Zhao-Hui,Chen, Hong-Bin
supporting information
p. 1530 - 1536
(2017/02/15)

Multicomponent Condensation Reactions via ortho-Quinone Methides
Iron(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo Diels - Alder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy(phenyl)methyl)phenols to access the desired ortho-quinone methide in a Diels - Alder condensation. The two-component condensation also afforded the corresponding benzopyran products in yields up to 97%. Taken together, the two- and three-component strategies using ortho-quinone methide intermediates provide efficient access to benzopyrans in good yields and selectivities.
Allen, Emily E.,Zhu, Calvin,Panek, James S.,Schaus, Scott E.
supporting information
p. 1878 - 1881
(2017/04/11)

Enantioselective Synthesis of 6,6-Disubstituted Pentafulvenes Containing a Chiral Pendant Hydroxy Group
Simple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl function of a 1,2-formylacetophenone, followed by cyclization of a resulting fulvene-stabilized carbanion with the formyl group, generates bicyclic chiral alcohols with initial er values up to 94:6. Exceptional enantio-enrichment of the resultant alcohols results upon crystallization—even near racemic samples spontaneously de-racemize. This enables new families of substituted cyclopentadienes that are both enantiomerically and diastereomerically pure to be rapidly attained.
Nouch, Ryan,Cini, Melchior,Magre, Marc,Abid, Mohammed,Diéguez, Montserrat,Pàmies, Oscar,Woodward, Simon,Lewis, William
supporting information
p. 17195 - 17198
(2017/11/27)

Phosphine-Catalyzed [4 + 2] Annulation of Allenoate with Sulfamate-Derived Cyclic Imines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate
A phosphine-catalyzed [4 + 2] cycloaddition of cyclic α-substituted allenoates with sulfamate-derived cyclic imines has been reported. Using dibenzylphenylphosphine as the nucleophilic catalyst, the reaction worked efficiently to yield various fused multicyclic heterocyclic compounds in high yields with excellent diastereoselectivities. It undergoes a new reaction mode involving γ′-carbon of α-substituted allenoate.
Mao, Biming,Shi, Wangyu,Liao, Jianning,Liu, Honglei,Zhang, Cheng,Guo, Hongchao
supporting information
p. 6340 - 6343
(2017/12/08)

Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group
The direct Pd-catalyzed ortho C-H hydroxylation of benzaldehydes was achieved using 4-chloroanthranilic acid as the transient directing group, 1-fluoro-2,4,6-trimethylpyridnium triflate as the bystanding oxidant, and p-toluenesulfonic acid as the putative oxygen nucleophile. The unusual C-H chlorination and polyfluoroalkoxylation reactions signaled the importance of external nucleophiles to the outcome of Pd(IV) reductive eliminations.
Chen, Xiao-Yang,Ozturk, Seyma,Sorensen, Erik J.
supporting information
p. 6280 - 6283
(2017/12/08)

Synthesis, characterization and cytotoxicity of platinum(II) complexes containing reduced amino acid ester Schiff bases
Nine platinum(II) complexes containing reduced amino acid ester Schiff bases were synthesized and characterized using spectroscopy (1H NMR, 13C NMR, infrared), elemental analysis and molar conductivity. The interaction of these complexes with salmon sperm DNA was investigated by means of ultraviolet and circular dichroism spectroscopies. The potential antitumor activity of all compounds was tested in vitro on HeLa and A549 tumor cell lines. Almost all the complexes exhibited better cytotoxic activity than cisplatin against these cell lines.
Yan, Qin-Qin,Yuan, Zhen,Liu, Guo-Jun,Lv, Zheng-Hua,Fu, Bin,Du, Jian-Long,Li, Li-Jun
(2017/05/22)

Synthesis characterization and cytotoxicity studies of platinum(II) complexes with reduced amino pyridine schiff base and its derivatives as ligands
A series of reduced amino pyridine Schiff base platinum(II) complexes were prepared as potential anticancer drugs, and characterized by NMR, IR spectroscopy, elemental analysis, and molar conductivity. UV and CD results showed the binding mode between these compounds and salmon sperm DNA may be intercalation. The cytotoxicity of these complexes was validated against A549, Hela, and MCF-7 cell lines by MTT assay. Some complexes exhibited better cytotoxic activity than cisplatin against Hela and MCF-7 cell lines.
Li, Li-Jun,Yan, Qin-Qin,Liu, Guo-Jun,Yuan, Zhen,Lv, Zhen-Hua,Fu, Bin,Han, Yan-Jun,Du, Jian-Long
p. 1081 - 1089
(2017/05/29)

Design and synthesis of novel Vitamin D-coumarin hybrids using microwave irradiation
A series of novel vitamin D-coumarin hybrids were synthesised by esterification of the corresponding coumarin-3-carboxylic acids and vitamin D or vitamin D CD-ring alcohol in CH2Cl2 under microwave irradiation. They were obtained in higher yields (from 64-81% up to 79-87%) and shorter reaction time (from 3 h down to 15 min), compared with earlier conventional methodologies. The structures of all the target compounds were confirmed by 1H NMR, 13C NMR and HRMS. This provides an attractive and alternative method for the preparation of high-value vitamin D-coumarin hybrids.
Zhang, Hengrui,Fang, Zhijie
p. 684 - 687
(2018/01/08)

Synthesis and antidepressant activity of 5-(benzo[b]furan-2-ylmethyl)-6-methylpyridazin-3(2H)-one derivatives
A new series of pyridazin-3-one derivatives were designed, synthesized and evaluated for their preclinical antidepressant effect on Swiss mice. Among the series, compounds 6c, 6d and 6f exhibited significant activity profile in forced swimming test. Compounds 6c and 6d were most efficacious, which at dose of 50 mg kg-1 reduced the time of immobility by 42.85 and 38.09 %, respectively, as compared to the standard drug fluoxetine which reduced the immobility time by 45.23 % at the dose of 32 mg kg-1. All the test and standard compounds were administered orally 60 min before the test. Interestingly, all active compounds did not cause any significant alteration of locomotor activity in mice as compared to control, indicating that the hybrids did not produce any motor impairment effects. The results indicate that pyridazin-3(2H)-one derivatives may have potential therapeutic value for the management of mental depression.
Boukharsa, Youness,Meddah, Bouchra,Tiendrebeogo, Ramata Yvette,Ibrahimi, Azeddine,Taoufik, Jamal,Cherrah, Yahia,Benomar, Ali,Faouzi, My El Abbes,Ansar, M'Hammed
p. 494 - 500
(2016/02/19)

Highly Selective Synthesis of Chlorophenols under Microwave Irradiation
Oxychlorination of various phenols is finished in 60 minutes with high efficiency and perfect selectivity under microwave irradiation. These reactions adopt copper(II) chloride (CuCl2) as the catalyst and hydrochloric acid as chlorine source instead of expensive and toxic ones. Oxychlorination of phenols substituted with electron donating groups (methyl, methoxyl, isopropyl, etc.) at ortho- and meta-positions is accomplished with higher conversion rates, lower reaction time, and excellent selectivity. A proposed reaction mechanism is deduced; one electron transfers from CuCl2 to phenol followed by the formation of tautomeric radical that can be rapidly captured by chlorine atom and converts into para-substituted product.
Xiong, Yawen,Duan, Hongdong,Meng, Xia,Ding, Zhaoyun,Feng, Weichun
(2016/06/14)

Efficient Co(OAc)2-catalyzed aerobic oxidation of EWG-substituted 4-cresols to access 4-hydroxybenzaldehydes
We reported an efficient ligand-free Co(OAc)2·4H 2O/NaOH/O2/ethylene glycol reaction system that enables selective aerobic oxidation of a wide range of substrates covering 2,6-di-EWG-, 2,3,6-tri-EWG-, 2-EWG-, and 2-EWG-6-EDG-substituted 4-cresols into the corresponding 4-hydroxybenzaldehydes. Based on the experimental investigations and well-defined p-benzoquinone methides, a plausible reaction mechanism was proposed. Considering the simplicity of the procedure and importance of the products, the methodology was expected to become a favorable and practical tool in related benzylic C(sp3)-H functionalization chemistry.
Jiang, Jian-An,Du, Jia-Lei,Liao, Dao-Hua,Wang, Zhan-Guo,Ji, Ya-Fei
supporting information
p. 1406 - 1411
(2014/03/21)

Synthesis, characterization and cytotoxicity studies of platinum(II) complexes with reduced amino acid ester Schiff-bases as ligands
A series of platinum(II) complexes with reduced amino acid esters Schiff-bases as ligands were prepared as potential anticancer agents and characterized by NMR, IR spectroscopy, elemental analysis and molar conductivity. These compounds were tested for their stability and DNA interaction with salmon sperm DNA by ultraviolet spectrum. The cytotoxicities of these complexes were validated against HL-60, BGC-823, Hela, and HepG2 cell lines by the MTT test. The complexes 5e and 5f exhibited better cytotoxic activity than cisplatin against HepG2 and BGC-823 cell lines, respectively.
Li, Li-Jun,Fu, Bin,Qiao, Yu,Wang, Cheng,Huang, Ying-Ying,Liu, Chuan-Chuan,Tian, Chao,Du, Jian-Long
p. 135 - 140
(2014/06/23)

NOVEL SUBSTITUTED PYRIDO-PIPERAZINONE DERIVATIVES AS GAMMA SECRETASE MODULATORS
The present invention is concerned with novel substituted pyrido-piperazinone derivatives of Formula (I) wherein R1, R2, R3, R4, R5, L, Z and X have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.
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(2014/08/06)

Cu(OAc)2·H2O-promoted tandem β-alkynyl elimination of α-or β-hydroxy propargylic alcohols and homocoupling of the resulting alkynyl species
α or β-hydroxy propargylic alcohols undergo tandem C(sp)-C(sp3) bond cleavage via β-alkynyl elimination and homocoupling of the resulted alkynyl species in the presence of Cu(OAc)2·H2O to produce the corresponding hydroxycarbonyl com
Xu, Xiangsheng,Huang, Zhenyong,Lu, Yanfeng
p. 546 - 549
(2013/10/22)

2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a new recyclable hypervalent iodine(III) reagent for chlorination and oxidation reactions
The synthesis of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine, as a new recyclable nonpolymeric analogue of (dichloroiodo)benzene, is achieved in two steps using 2,4,6-trichloro-1,3,5-triazine and 4-iodophenol. The application of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine for the chlorination reaction of various activated arenes, olefin, and 1,3-diketone is demonstrated. The reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5- triazine from the reaction mixture due to its practical insolubility in methanol. Georg Thieme Verlag Stuttgart, New York.
Thorat, Prerana B.,Bhong, Bhagyashree Y.,Karade, Nandkishor Y.
supporting information
p. 2061 - 2066
(2013/10/21)

Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant
A new natural product isolated from the leaves of the plant Anthurium aripoense found in Trinidad is shown by spectroscopic analysis and total synthesis to be 2′,5,6′-trichloro-2,3′-dihydroxybibenzyl, a structure unprecedented in a higher plant. The Royal Society of Chemistry 2013.
Aitken, R. Alan,Bouquet, Jaufret,Frank, Julia,Gidlow, Anna L. G.,Powder, Yomica L.,Ramsewak, Russel S.,Reynolds, William F.
p. 7230 - 7232
(2013/07/05)

SMALL MOLECULE MALARIAL ALDOLASE-TRAP ENHANCERS AND GLIDEOSOME INHIBITORS
In one aspect, the present invention relates to a method of identifying compounds useful in modifying the activity of Aldolase. The method includes providing a first model comprising Aldolase or residues of the amino acid sequence corresponding to SEQ ID NO: 1 said residues being at amino acid positions selected from the group consisting of 10-13, 26, 27, 29, 30, 31, 32, 33, 37, 39, 40, 41, 43, 44, 47, 48, 51, 52, 60, 63, 66, 79, 84, 85, 92, 93, 103, 106-109, 112-117, 138, 142, 146, 148, 151, 153, 179, 182, 183, 185, 186, 194, 196, 197, 198, 199, 208, 226-228, 231- 269, 270, 272, 277-283, 285-289, 294, 295, 297-299, 301-304, 306-310, 312, 313, 316, 317, 319, 321, 323, 326, 330, 344, 345, and 347, providing one or more candidate compounds, evaluating contact between the candidate compounds and the first model to determine which of the one or more candidate compounds have an ability to bind to and/or fit in the first model, and identifying compounds which, based on said evaluating, have the ability to bind to and/or fit in the first model as compounds potentially useful for modifying the activity of Aldolase. The present invention also discloses compounds and compositions which modify the activity of Aldolase, or a complex between Aldolase and TRAP. Methods of treating or preventing malaria, or an infection by apicomplexan organisms are also disclosed.
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(2013/05/21)

Synthesis of chromones through LiOtBu/air-mediated oxidation and regioselective cyclization of o-hydroxyphenyl propargyl carbinols
A cascade oxidative cyclization reaction for the synthesis of chromone derivatives was developed by using LiOtBu as a mediator and air as an oxidant. The reaction was carried out without the assistance of a transition metal under mild conditions to afford the chromones in good yields with high regioselectivities. A tandem reaction for the synthesis of various chromones was developed. LiOtBu was used as a mediator and air was used as a clean oxidant. The reaction generally showed high regioselectivity under mild conditions. Extensive research showed that dehydrogenative oxidation of the alcohols under strongly basic conditions was the crucial step, and Li+ was also found to play an important role in this process. Copyright
Zhang, Shuai,Wan, Changfeng,Wang, Qiang,Zhang, Baiqun,Gao, Lingfeng,Zha, Zhenggen,Wang, Zhiyong
supporting information
p. 2080 - 2083
(2013/05/09)

Pd(II)-catalyzed asymmetric Wacker-type cyclization for the preparation of 2-vinylchroman derivatives with biphenyl tetraoxazoline ligands
This article describes an efficient method for the preparation of chiral chroman derivatives by the Pd(II)-catalyzed asymmetric Wacker-type cyclization using a chelation-induced axially chiral tetraoxazoline ligand. Under the optimized conditions, up to 80% yield and up to 92% ee were obtained. This is the first example to utilize o-trisubstituted 3-butenylphenols as substrates in such transformation.
Liu, Qingchuan,Wen, Ke,Zhang, Zhenfeng,Wu, Zhengxing,Zhang, Yong Jian,Zhang, Wanbin
experimental part
p. 5209 - 5215
(2012/08/08)

Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes
A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.
Singh, Parvinder Pal,Thatikonda, Thanusha,Kumar, K. A. Aravinda,Sawant, Sanghapal D.,Singh, Baldev,Sharma, Amit Kumar,Sharma,Singh, Deepika,Vishwakarma, Ram A.
experimental part
p. 5823 - 5828
(2012/09/05)

PREPARATION OF BENZOFURANS AND USE THEREOF AS SYNTHETIC INTERMEDIATES
The present invention provides several synthetic methods for preparing N-(2-butylbenzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide, a compound of formula (3), an intermediate in the preparation of Dronedarone. The present invention further provides a process for preparing Dronedarone, comprising the steps of converting 2-butyl-5-bis(methanesulfon)-amidobenzofuran of formula (3) to Dronedarone, wherein the 2-butyl-5-bis(methanesulfon)-amidobenzofuran of formula (3) is prepared by the processes of the present invention.
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Page/Page column 30

(2011/09/15)

Efficient one-pot synthesis of ethyl [2-(2H-Chromene-3yl)-4-oxo-L,3- thiazolidin-3-yl]acetates
Ethyl [2-(2H-chromene-3yl)-4-oxo-1,3-thiazolidin-3yl]acetates (6a-e) were synthesized in a single pot by the reaction of 2H-3-chromenecarbaldehydes (3a-e), glycine ethyl ester hydrochloride (4), and mercaptoacetic acid (5) in diisopropylethylamine/benzene under refluxing conditions in a Dean-Stark trap.
Reddy, S. Satyanarayana,Krupadanam, G. L. David
body text
p. 1305 - 1311
(2010/06/20)

Syntheses, characterization, and ethylene polymerization of titanium and zirconium complexes with [N, O] ligands
Bidentate monoanionic ligands 2-(benzo[d]thiazol-2-yl) phenol (La), 2-(benzo[d]thiazol-2-yl)-6-methylphenol (Lb), 2-(benzo[d]thiazol-2-yl)-6-tert- butyl-4-methylphenol (Lc), 2-(benzo[d]thiazol-2-yl)-6-chlorophenol (Ld), and 2-(benzo[d]thiazol-2-yl)-4-chlorophenol (Le) have been synthesized. Reactions of TiCl4(THF)2 or ZrCl4 with La-Le afford the corresponding titanium complexes Ti[ON]2RCl2 [R = 6-Me (2b); R = 4-Me-6-But (2c)], and zirconium complexes Zr[ON]2RCl2 [R = H (3a); R = 6-Me (3b); R = 4-Me-6-But (3c); R = 6-Cl (3d); R = 4-Cl (3e)], and Zr[ON R]HCl4·THF [R = 6-Me (4b)], respectively. Complexes 2a-4b were characterized by IR, 1H NMR spectra and elemental analysis. The molecular structures of La, 2b, 2c, 3b, 3c and 4b have been characterized by single-crystal X-ray diffraction analyses. The effect of steric hindrance and the coordination metal on the structure of the products has been investigated. When activated by excess methylaluminoxane (MAO), 2b and 2c, 3a-3e and 4b can be used as catalysts for ethylene polymerization and exhibit moderate to good activities.
Jia, Ai-Quan,Jin, Guo-Xin
scheme or table
p. 8838 - 8845
(2010/02/16)

An unusual reaction of benzalaminoacetals in trifluoroacetic acid: Facile synthesis of 2-benzylpyrazines
(Chemical Equation Presented) Benzalaminoacetals (1), upon refluxing with trifluoroacetic acid, lead to 2-benzylpyrazines, rather than the expected isoquinolines. This unusual reaction represents another useful way to prepare a variety of 2-benzylpyrazines from the corresponding benzaldehydes.
Augustine, John Kallikat,Naik, Yanjerappa Arthoba,Mandal, Ashis Baran,Kundapur, Umesha
p. 1176 - 1179
(2008/09/18)

Asymmetric Henry reaction catalyzed by a copper tridentate chiral schiff-base complex
A series of copper-tridentate chiral Schiff-base complexes were prepared and employed in an asymmetric Henry reaction, affording the corresponding adducts in good yields and with high enantioselectivities (up to 96% ee).
Lai, Guoyin,Wang, Sujing,Wang, Zhiyong
p. 1813 - 1819
(2008/12/22)

Novel synthesis of oxathiocine derivatives by Wittig olefination and intramolecular Heck reaction via an 8-endo-trig cyclization
Syntheses of hitherto unreported heterocycles, such as oxathiocine derivatives, in excellent yields, and a doubly cyclized oxathiocine derivative, through a Wittig olefination and intramolecular Heck reaction sequence via an unusual 8-endo-trig cyclization, are reported. Georg Thieme Verlag Stuttgart.
Majumdar, Krishna C.,Chattopadhyay, Buddhadeb,Sinha, Biswajit
experimental part
p. 3857 - 3863
(2009/06/17)

Synthesis of substituted salicylamines and dihydro-2H-1,3-benzoxazines
Phenols were converted to their magnesium salts with the MgCl2-Et3N base system and subsequently reacted with Eschenmoser's salt, affording N,N-dimethyl substituted benzylamines in high to excellent yields. A series of mono N-substituted benzylamines were prepared in one-pot syntheses by ortho-formylation of phenols to corresponding salicylaldehydes, which in turn reacted with amines to imines. The imines were subsequently reduced to mono N-substituted benzylamines. Some of these benzylamines were further converted, without work-up, to mono N-substituted dihydro-2H-1,3-benzoxazines.
Anwar, Hany F.,Skatteb?l, Lars,Hansen, Trond Vidar
p. 9997 - 10002
(2008/02/13)

Synthesis of substituted 2-hydroxyaryl aldehydes by the microwave-induced Reimer-Tiemann reaction
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Vibhute, Yeshwant B.,Lonkar, Subhash M.,Sayyed, Mudassar A.,Baseer, Mohammad A.
p. 51 - 51
(2007/10/03)

Synthesis of chromanones: A novel palladium-catalyzed Wacker-type oxidative cyclization involving 1,5-hydride alkyl to palladium migration
A series of 2-methylchromanone derivatives have been prepared by using a novel palladium-catalyzed Wacker-type oxidative cyclization, in which a 1,5-hydride alkyl to palladium migration and a direct chirality transfer were involved. The Royal Society of Chemistry.
Zhang, Zuhui,Pan, Chongfeng,Wang, Zhiyong
p. 4686 - 4688
(2008/10/09)

Synthesis and reduction of 5-halo-and 5-nitro-1-(benzofuran-3-yl)-2- phenylethanones
Novel 1-(2-alkylbenzofuran-3-yl)-2-(4-methoxyphenyl)ethanones having a halogen or nitro group in position 5 of the benzofuran ring were synthesized starting with the corresponding 2-(2-formylphenoxy)alkanoic acids. 1-(2-Alkylbenzofuran-3-yl)-2-phenylethanols containing bromine or chlorine atom were prepared in high yields by reduction of the corresponding ethanones with lithium aluminum hydride. Selective catalytic reduction of nitro 1-(2-alkylbenzofuran-3-yl)-2-(4-methoxyphenyl)ethanones to the corresponding amino compounds under Pd/C in room temperature was achieved.
Kwiecien,Szychowska
p. 1002 - 1009
(2008/09/16)

One-pot synthesis of substituted catechols from the corresponding phenols
Phenols are converted to salicylaldehydes with paraformaldehyde, MgCl 2-Et3N in THF, and when subsequently treated with aqueous NaOH and H2O2 afford the corresponding catechols. The sequence is conveniently carried out as a one-pot procedure.
Hansen, Trond Vidar,Skatteb?l, Lars
p. 3357 - 3358
(2007/10/03)

One-pot synthesis of ortho-hydroxycinnamate esters
Phenols are converted to salicylaldehydes with paraformaldehyde, MgCl 2-Et3N in THF, and subsequent treatment with methyl (triphenylphosphoranylidene)acetate gave the corresponding methyl ortho-hydroxycinnamate derivatives. The sequence is conveniently carried out as a one-pot procedure.
Anwar, Hany F.,Skatteb?l, Lars,Skramstad, Jan,Hansen, Trond Vidar
p. 5285 - 5287
(2007/10/03)

Non-metallocene compounds, method for the production thereof and use of the same for the polymerisation of olefins
The invention relates to a method for producing special transition metal compounds, to novel transition metal compounds and to the use of the same for the polymerisation of olefins.
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(2008/06/13)

Method for producing optically active salicylaldimine copper complex
There is provided a method for producing an optically active salicylaldimine copper complex, which method is characterized in that an optically active amino alcohol compound represented by the following formula (1) is reacted with copper hydroxide (II) in an organic solvent. wherein R1 and R2 which are the same or different, each represent lower alkyl groups and the like which may be substituted, X1 and X2 which are the same or different, each represent a hydrogen atom, lower alkyl groups and the like, and the symbol * designates an asymmetric carbon atom.
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(2008/06/13)

Convenient Method for the ortho-Formylation of Phenols
Phenolic derivatives are formylated selectively ortho to the hydroxy group by paraformaldehyde with magnesium dichloride-triethylamine as base. With alkyl-substituted phenols excellent yields of the corresponding salicylaldehyde derivatives were obtained. Similar results were obtained with chloro-substituted phenols and with 3- and 4-methoxyphenol, while 2-methoxyphenol was unreactive. A good yield of methyl 3-formyl-4-hydroxybenzoate was obtained by this method as well, but generally phenols with electron-attracting groups reacted sluggishly; the long reaction times required caused the formation of by-products, particularly MOM-derivatives of the phenols.
Hofslokken, Nini U.,Skattebol, Lars
p. 258 - 262
(2007/10/03)

Intramolecular propargyl transfer reaction catalyzed by electrogenerated nickel complexes
The intramolecular transfer of the propargyl group of aryl propargyl ethers to a carbonyl group can be effected by a nickel-catalyzed electrochemical reaction. Homopropargyl alcohols with 2-hydroxyphenyl substituents can be obtained, using a magnesium anode in single compartment cells.
Franco, Delphine,Dunach, Elisabet
p. 2951 - 2954
(2007/10/03)

Prodrugs - Part 1. Formylphenyl esters of aspirin
The synthesis and study of a novel series of potential prodrugs of aspirin is reported. 2-, 3- and 4-formylphenyl aspirins, as well as a series of 4-substituted 2-formylphenyl aspirins, have been prepared. A study of their alkaline hydrolysis indicates that these compounds act as true prodrugs of aspirin which hydrolyse to aspirin and the formylphenol. The rates of hydrolysis and activation parameters indicate that hydrolysis of the 2-formylphenyl esters employs an intramolecular catalytic route.
Bowden,Huntington,Powell
p. 987 - 993
(2007/10/03)