Synthesis of dibenzofurans directly from aryl halides and ortho-bromophenols via one-pot consecutive SNAr and intramolecular palladium-catalyzed aryl-aryl coupling reactions.

Abstract:

:A series of dibenzofurans were efficiently and conveniently synthesized via one-pot consecutive C(sp(2))-O bond formation reaction (SNAr) in the presence of anhydrous K(2)CO(3), followed by C(sp(2))-C(sp(2)) bond formation reaction (intramolecular palladium-catalyzed aryl-aryl coupling reaction) between aryl halides and ortho-bromophenols. The desired dibenzofurans were obtained in 32-99% isolated yields.

authors

Xu H,Fan LL

doi

10.1248/cpb.56.1496

subject

Has Abstract

pub_date

2008-10-01 00:00:00

pages

1496-8

issue

10

eissn

0009-2363

issn

1347-5223

pii

JST.JSTAGE/cpb/56.1496

journal_volume

56

pub_type

杂志文章
  • Spectroscopic analysis of charge transfer complex formation between neuroleptics and iodine.

    abstract::Molecular interactions between iodine and various neuroleptics were investigated by UV/Vis spectroscopy. Iodine was found to form charge transfer complexes in a 1:1 stoichiometry and of n-sigma type with these molecules. The values of the formation constants Kc of these iodinated complexes indicate a strong donor-acce...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.37.151

    authors: Comby F,Jambut-Absil AC,Buxeraud J,Raby C

    更新日期:1989-01-01 00:00:00

  • Novel Orally Disintegrating Tablets Produced Using a High-Pressure Carbon Dioxides Process.

    abstract::It is well known that high-pressure carbon dioxide (CO2) lowers the glass transition temperature (Tg) of polymers. We therefore investigated whether Tg depression of high-pressure CO2 results in interparticle bridging of a polymer and the tablet characteristics that makes the manufacture of an orally disintegrating ta...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c18-00220

    authors: Kobayashi M,Shinozuka D,Kondo H,Sako K,Otake K

    更新日期:2018-01-01 00:00:00

  • Antisweet natural products. VIII. Structures of hodulosides VI--X from Hovenia dulcis Thunb. var. tomentella Makino.

    abstract::From the Fresh leaves of Hovenia dulcis Thunb. var. tomentella Makino, five five new dammarane glycosides named hodulosides VI-X (1-5) were isolated. Their structures were determined on the basis of chemical and spectral evidence. Hodulosides VII-X showed antisweet activities. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1722

    authors: Yoshikawa K,Nagai Y,Yoshida M,Arihara S

    更新日期:1993-10-01 00:00:00

  • Possible mechanism of the stimulatory effect of Artemisia leaf extract on the proliferation of cultured endothelial cells: involvement of basic fibroblast growth factor.

    abstract::To investigate the possible mechanism of the stimulatory effect of a hot water extract from Artemisia leaf (Artemisia princeps PANPANINI) (AFE) on the proliferation of endothelial cells, cells from bovine aorta were cultured for 72 h in RPMI1640 medium supplemented with 10% fetal calf serum in the presence of 5 microg...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.38.2494

    authors: Kaji T,Kaga K,Miezi N,Hayashi T,Ejiri N,Sakuragawa N

    更新日期:1990-09-01 00:00:00

  • The structure of a new cardenolide diglycoside and the biological activities of eleven cardenolide diglycosides from Nerium oleander.

    abstract::A new cardenolide diglycoside (1) was isolated from Nerium oleander together with ten known cardenolide diglycosides 2-11. The structure of compound 1 was established on the basis of their spectroscopic data. The in vitro anti-inflammatory activity of compounds 1-11 was examined on the basis of inhibitory activity aga...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.59.371

    authors: Zhao M,Bai L,Toki A,Hasegawa R,Sakai J,Hasegawa T,Ogura H,Kataoka T,Bai Y,Ando M,Hirose K,Ando M

    更新日期:2011-01-01 00:00:00

  • Characterization of sodium hypochlorite degradation of beta-glucan in relation to its metabolism in vivo.

    abstract::Soluble (SSG, beta-1,3-D-glucan obtained from the culture filtrates of a fungus, Sclerotinia sclerotiorum IFO 9395) and particulate (zymosan) beta-glucans were oxidized by sodium hypochlorite (NaClO), and the oxidized products were analyzed by gel filtration and ion-exchange chromatographies and by limulus G-test to s...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.2137

    authors: Miura NN,Ohno N,Adachi Y,Yadomae T

    更新日期:1996-11-01 00:00:00

  • Relationship between effects of phenolic compounds on the generation of free radicals from lactoperoxidase-catalyzed oxidation of NAD(P)H or GSH and their DPPH scavenging ability.

    abstract::The influence of various phenolic compounds on the lactoperoxidase (LPO)/hydrogen peroxide (H2O2)-catalyzed oxidation of biochemical reductants such as reduced beta-nicotinamide adenine dinucleotide (NADH), reduced beta-nicotinamide adenine dinucleotide phosphate (NADPH) or reduced glutathione (GSH) was investigated b...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.299

    authors: Ueda J,Tsuchiya Y,Ozawa T

    更新日期:2001-03-01 00:00:00

  • Production of secondary metabolites by freshwater cyanobacteria.

    abstract::Freshwater cyanobacteria produce lethal toxins such as microcystins and anatoxins. During the purification of microcystins in bloom samples we found that a toxic cyanobacterium produced not only microcystins but also other types-peptides in early 1990. Since then we have isolated approximately thirty peptides from fre...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.52.889

    authors: Harada K

    更新日期:2004-08-01 00:00:00

  • Synthesis and pharmacological activities in mice of halogenated delta 9-tetrahydrocannabinol derivatives.

    abstract::Seven halogenated derivatives of delta 9-tetrahydrocannabinol (delta 9-THC, 1) substituted on the aromatic ring at the 2 and/or 4 position, 2 (4)-fluoro- (2), 2,4-difluoro- (3), 2-chloro- (4), 2-bromo- (5), 2,4-dibromo- (6), 2-iodo- (7) and 2,4-diiodo-delta 9-THC (8) were synthesized and pharmacological effects such a...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.46.1462

    authors: Usami N,Kobana K,Yoshida H,Kimura T,Watanabe K,Yoshimura H,Yamamoto I

    更新日期:1998-09-01 00:00:00

  • Solution-phase automated synthesis of tripeptide derivatives.

    abstract::An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, di...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.49.1138

    authors: Kuroda N,Hattori T,Kitada C,Sugawara T

    更新日期:2001-09-01 00:00:00

  • The combination effect of L-arginine and NaCl on bitterness suppression of amino acid solutions.

    abstract::The purpose of the present study was to quantify the degree of suppression of the bitterness of two amino acids (L-isoleucine (L-Ile), and L-phenylalanine (L-Phe)) which could be achieved by the addition of various test chemicals, and to examine the mechanism of this bitterness suppression. The test chemicals used wer...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.52.172

    authors: Ogawa T,Nakamura T,Tsuji E,Miyanaga Y,Nakagawa H,Hirabayashi H,Uchida T

    更新日期:2004-02-01 00:00:00

  • Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane.

    abstract::Total synthesis of the biologically important axane sesquiterpenes, gleenol (1) and axenol (2), was accomplished through a readily available spiro[4.5]decane. The key features of the synthesis of 1 and 2 include Claisen rearrangement to afford the multi-functionalized spiro[4.5]decane 4 as a single diastereomer in exc...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.55.1606

    authors: Nakazaki A,Era T,Kobayashi S

    更新日期:2007-11-01 00:00:00

  • Tandem enzymatic resolution yielding L-alpha-aminoalkanedioic acid omega-esters.

    abstract::The tandem action of serine protease (alpha-chymotrypsin or subtilisin BPN') and Aspergillus genus aminoacylase on racemic N-acetyl-alpha-aminoalkanedioic acid alpha,omega-diester produced L-alpha-aminoalkanedioic acid omega-ester in good yield and high optical purity. L-alpha-Aminosuberic acid omega-ester thus obtain...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.44.212

    authors: Nishino N,Arai T,Ueno Y,Ohba M

    更新日期:1996-01-01 00:00:00

  • Synthetic studies of vitamin D analogs. XXIV. Synthesis of active vitamin D3 analogs substituted at the 2 beta-position and their preventive effects on bone mineral loss in ovariectomized rats.

    abstract::Analogs related to 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D3 (ED-71) (4), oxa-type and carba-type analogs of vitamin D3 bearing substituents at the 2 beta-position of 1 alpha,25-dihydroxyvitamin D3 (1), were synthesized from the alpha-epoxides (6 and 13). Three analogs, ED-71 (4) and two carba-type anal...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.45.1626

    authors: Ono Y,Watanabe H,Shiraishi A,Takeda S,Higuchi Y,Sato K,Tsugawa N,Okano T,Kobayashi T,Kubodera N

    更新日期:1997-10-01 00:00:00

  • Effect of grinding with hydroxypropyl cellulose on the dissolution and particle size of a poorly water-soluble drug.

    abstract::A new benzofuroquinoline derivative, 3,9-bis(N,N-dimethylcarbamoyloxy)-5H-benzofuro[3,2-c]quinoli ne-6-one (KCA-098), shows poor oral absorption due to practical insolubility in water. In this study, a co-grinding technique employing a water-soluble polymer was used for improvement of the dissolution rate of KCA-098. ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.47.1311

    authors: Yamada T,Saito N,Imai T,Otagiri M

    更新日期:1999-09-01 00:00:00

  • Importance of Proton-Coupled Electron Transfer from Natural Phenolic Compounds in Superoxide Scavenging.

    abstract::The superoxide O2(·-) scavenging reaction of (+)-catechin (Cat), quercetin (Que), rutin, and α-tocopherol (α-TOH) as natural phenolic compounds is investigated on the basis of electrochemical and ESR spectral measurements with the aid of density functional theory (DFT) calculations. Reversibility of the O2/O2(·-) redo...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00447

    authors: Nakayama T,Uno B

    更新日期:2015-01-01 00:00:00

  • Development of new cycloaddition reactions based on the unique reactivity of unsaturated hydrocarbons.

    abstract::We discovered that the reactivity of some conjugated and electron-deficient hydrocarbons was quite different in the presence of transition metal catalysts. In this review we report our development and applications of the highly selective palladium and nickel-catalyzed cycloaddition reactions of unsaturated hydrocarbon...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.53.1069

    authors: Saito S

    更新日期:2005-09-01 00:00:00

  • Abietane diterpenoids from the barks of Cryptomeria japonica.

    abstract::From the bark of Cryptomeria japonica were isolated sugikurojins I (1) and J (2), and an abietane derivative (3) was obtained for the first time as a natural product. These structures were elucidated primarily through extensive NMR experiments. Sugikurojin I (1) has a unique skeleton incorporating an abietane diterpen...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.54.574

    authors: Yoshikawa K,Suzuki K,Umeyama A,Arihara S

    更新日期:2006-04-01 00:00:00

  • Efficient identification and quantification of peptides containing nitrotyrosine by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry after derivatization.

    abstract::Protein nitration at tyrosine residues proceeds to form 3-nitrotyrosine; this product is today used as a biomarker of nitrative stress. We have developed an efficient method with which to identify nitrated peptides and to quantify protein nitration levels in different biological samples by a combination of the chemica...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.58.488

    authors: Tsumoto H,Taguchi R,Kohda K

    更新日期:2010-04-01 00:00:00

  • Design, Synthesis and Antiproliferative Evaluation of Novel Disulfides Containing 1,3,4-Thiadiazole Moiety.

    abstract::A series of novel disulfides containing 1,3,4-thiadiazole moiety were designed, synthesized, and the structures of all products were identified by spectral data (IR, NMR, and high resolution (HR)-MS). Their in vitro antiproliferative activities were evaluated using 2-(2-methoxy-4-nitro-phenyl)-3-(4-nitro-phenyl)-5-(2,...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c17-00485

    authors: Zhang S,Liu XJ,Tang R,Wang HX,Liu HY,Liu YM,Chen BQ

    更新日期:2017-01-01 00:00:00

  • Pyrrole Oligoglycosides from the Starfish Acanthaster planci Suppress Lipopolysaccharide-Induced Nitric Oxide Production in RAW264.7 Macrophages.

    abstract::Two new pyrrole oligoglycosides, plancipyrrosides A and B (1 and 2), were isolated from methanol extract of the Vietnamese starfish Acanthaster planci using various chromatographic procedures. Their structures were elucidated by spectroscopic methods including one and two dimensional (1D- and 2D)-NMR and Fourier trans...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c16-00585

    authors: Vien LT,Hanh TT,Huong PT,Dang NH,Thanh NV,Lyakhova E,Cuong NX,Nam NH,Kiem PV,Kicha A,Minh CV

    更新日期:2016-11-01 00:00:00

  • Antimutagenic constituents from the thorns of Gleditsia sinensis.

    abstract::Antimutagenic activity-guided fractionation of an extract prepared from the thorns of Gleditsia sinensis LAM. led to the isolation of one triterpenoid and four steroids, which were identified as D:C-friedours-7-en-3-one (1), stigmast-4-ene-3,6-dione (2), stigmastane-3,6-dione (3), stigmasterol (4), and beta-sitosterol...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.53.561

    authors: Lim JC,Park JH,Budesinsky M,Kasal A,Han YH,Koo BS,Lee SI,Lee DU

    更新日期:2005-05-01 00:00:00

  • Comparative molecular field analysis study of stilbene derivatives active against A549 lung carcinoma.

    abstract::A series of 43 stilbene derivatives that showed cytotoxicity against human lung carcinoma (A549) was analyzed using comparative molecular field analysis (CoMFA) for defining the hypothetic pharmacophore model. The polyoxylated stilbenes were found to be active inhibitors of tubulin polymerization. Several cis-stilbene...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.51.516

    authors: Kim S,Min SY,Lee SK,Cho WJ

    更新日期:2003-05-01 00:00:00

  • Prediction of the stability of imipenem in intravenous mixtures.

    abstract::The purpose of this study was to predict the stability of imipenem in a mixed infusion. The hydrolysis of imipenem in aqueous solution was found to be accelerated by pH, and by increasing concentrations of sodium bisulfite (SBS) and L-cysteine. Equations were derived for the degradation rate constants (k(obs)) of pH, ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c12-00427

    authors: Yoshida M,Takasu Y,Shimizu K,Asahara K,Uchida T

    更新日期:2013-01-01 00:00:00

  • Effect of Chaenomeles sinensis Extract on Choline Acetyltransferase Activity and Trimethyltin-Induced Learning and Memory Impairment in Mice.

    abstract::The aim of this study was to search for a novel choline acetyltransferase (ChAT) activator from plants traditionally grown in Korea. An ethanol extract from Chaenomeles sinensis Koehne showed the highest ChAT-activating effect in vitro in an assay that used human neuroblastoma cells and [(14)C]acetyl-CoA. The active c...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.c15-00559

    authors: Kwon YK,Choi SJ,Kim CR,Kim JK,Kim HK,Choi JH,Song SW,Kim CJ,Park GG,Park CS,Shin DH

    更新日期:2015-01-01 00:00:00

  • Spectrophotometric and atomic absorption determination of ramipril, enalapril maleate and fosinopril through ternary complex formation with molybdenum (V)-thiocyanate (Mo(V)-SCN).

    abstract::Three different sensitive and accurate spectroscopic procedures were developed for the determination of three angiotensin-converting enzyme inhibitors, namely, ramipril, enalapril maleate and fosinopril. The first two spectrophotometric (extractive and non-extractive) procedures were based on ternary complex formation...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.56.1521

    authors: Baraka MM,El-Sadek M,Moussa EM,Abd-Alaty NM

    更新日期:2008-11-01 00:00:00

  • Synergistic action of phenolic signal compounds and carbohydrates in the induction of virulence gene expression of Agrobacterium tumefaciens.

    abstract::Virulence (vir) gene expression of Agrobacterium tumefaciens is activated by plant phenolic compounds such as alpha-hydroxyacetosyringone (HOAS), acetosyringone (AS), methyl syringate, coniferyl alcohol and sinapyl alcohol. Inositol was found to be a potentiating factor of vir-inducing activity, which enhanced the vir...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.39.2613

    authors: Song YN,Shibuya M,Ebizuka Y,Sankawa U

    更新日期:1991-10-01 00:00:00

  • Synthesis and biological activities of metabolites of mosapride, a new gastroprokinetic agent.

    abstract::In order to confirm the proposed structures of two metabolites 3 and 4 of the gastroprokinetic agent mosapride [4-amino-5-chloro-2-ethoxy-N-([4-(4-fluorobenzyl)-2-morpholinyl] methyl)benzamide, 2], the compounds were synthesized and their biological activity was examined. The structures of the metabolites were confirm...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.43.699

    authors: Kato S,Morie T,Yoshida N

    更新日期:1995-04-01 00:00:00

  • 1,4:3,6-Dianhydrohexitol nitrate derivatives. II. Synthesis and antianginal activity of aryl- or arylcarbonylpiperazine derivatives.

    abstract::A series of 5-(4-aryl- or 4-arylcarbonylpiperazin-1-yl)-5-deoxy-1,4: 3,6-dianhydro-L-iditol 2-nitrates was prepared in order to obtain orally active, nitrate-type vasodilators with reduced side effects. Our drug design was based on a small reduction in the lipophilicity compared to that of 5-deoxy-5-[4-(3-phenylthiopr...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章

    doi:10.1248/cpb.41.1100

    authors: Hayashi H,Ikeda J,Kubo K,Moriyama T,Karasawa A,Suzuki F

    更新日期:1993-06-01 00:00:00

  • Total synthesis of biologically active natural products based on highly selective synthetic methodologies.

    abstract::Total syntheses of structurally and biologically intriguing natural products relying on new synthetic methodologies are described. This article features cinchona alkaloid-catalyzed asymmetric Morita-Baylis-Hillman reactions, heterocycle syntheses based on rhodium-catalyzed C-H amination and indium-catalyzed Conia-ene ...

    journal_title:Chemical & pharmaceutical bulletin

    pub_type: 杂志文章,评审

    doi:10.1248/cpb.c14-00474

    authors: Hatakeyama S

    更新日期:2014-01-01 00:00:00