Jie Tang

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Name: 汤杰; Jie Shang

Organization: East China Normal University , China

Department: Department of Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

Polymer

Stimuli Responsive Polymers Stimuli Responsive Polymers Photo Responsive Polymers

Chemicals
References

Palladium-catalyzed cross-coupling of aryl chlorides with O, N-chelate stabilized diarylborinates

Co-reporter:Nan Zhang, Chen Wang, Gang Zou, Jie Tang

Journal of Organometallic Chemistry 2017 Volume 842(Volume 842) pp:

Publication Date(Web):1 August 2017

DOI:10.1016/j.jorganchem.2017.05.013

•O, N-chelate stabilized diarylborinates prepared and fully characterized.•Cross-coupling of aryl chlorides with O, N-chelate stabilized diarylborinates achieved.•A six-membered O, N-chelate to B balances the stability and reactivity of diarylborinates.•Structural effects from both aryl chlorides and diarylborinates investigated.A series of O, N-chelated diarylborinates have been prepared and tested as arylboron counterpart alternative to oxygen-labile diarylborinic acids in palladium catalyzed Suzuki coupling of aryl chlorides. 3-Dimethylaminopropyl diarylborinates (B-5a), featuring a six-membered O, N-chelated boron ring that was confirmed by single crystal X-ray diffraction, displayed a delicately balanced stability and reactivity. Their cross-coupling with structurally various aryl chlorides could be effected as efficiently as that of the parent diarylborinic acids by using 0.1∼1mol% Pd(OAc)2/IPr/P(OPh)3 as catalyst system, to provide the corresponding biaryls in good to excellent yields.Download high-res image (119KB)Download full-size image

Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids

Co-reporter:Changwei Guan, Yuanyuan Feng, Gang Zou, Jie Tang

Tetrahedron 2017 Volume 73, Issue 49(Issue 49) pp:

Publication Date(Web):7 December 2017

DOI:10.1016/j.tet.2017.10.043

N-Arylation of (benz)imidazoles and amines with diarylborinic acids as cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric hindrance appeared to affect the copper-catalyzed N-arylation using the high-order arylboron reagent more significantly than the electronic factors, especially for low reactive anilines and aliphatic amines.Download high-res image (99KB)Download full-size image

Development of Novel Alkoxyisoxazoles as Sigma-1 Receptor Antagonists with Antinociceptive Efficacy

Co-reporter:Hao Sun; Min Shi; Wei Zhang; Yue-Ming Zheng; Ya-Zhou Xu; Jun-Jie Shi; Ting Liu; Hendra Gunosewoyo; Tao Pang; Zhao-Bing Gao; Fan Yang; Jie Tang;Li-Fang Yu

Journal of Medicinal Chemistry 2016 Volume 59(Issue 13) pp:6329-6343

Publication Date(Web):June 16, 2016

DOI:10.1021/acs.jmedchem.6b00571

A novel series of sigma (σ) receptor ligands based on an alkoxyisoxazole scaffold has been designed and synthesized. Preliminary receptor binding assays identified highly potent (Ki < 1 nM) and selective σ1 ligands devoid of binding interactions with the monoamine transporters DAT, NET, and SERT. In particular, compound 53 was shown to possess significant antinociceptive activity in the mouse formalin-induced inflammation pain model when administered intraperitoneally at 40 and 80 mg/kg. Initial pharmacokinetics evaluation indicated an excellent brain exposure following oral dosing in mice, suggesting that further investigation into the use of alkoxyisoxazoles as σ1 ligands for antinociception is warranted. This study supports the notion that selective σ1 antagonism could be a useful strategy in the development of novel antipain therapy.

Tandem Demethylation/Annulation/Oxidation of 2,3-Bis(2-methoxyphenyl)-3-oxopropanals for One-Pot Construction of Coumestans

Co-reporter:Jiefeng Zhang;Jiakun Qiu;Chunmei Xiao;Lifang Yu;Fan Yang

European Journal of Organic Chemistry 2016 Volume 2016( Issue 20) pp:3380-3385

Publication Date(Web):

DOI:10.1002/ejoc.201600122

A convenient and practical approach to coumestans has been successfully developed by using a one-pot tandem demethylation/annulation/oxidation reaction sequence that employs easily accessible 2,3-bis(2-methoxyphenyl)-3-oxopropanals as the starting material. This synthetic protocol provided a variety of coumestan derivatives in good to excellent yields under mild conditions. The exploration of biologically active coumestan compounds is a potential application of this synthetic method.

Efficient construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides

Co-reporter:Sheng Wang, Chao Zhao, Ting Liu, Lifang Yu, Fan Yang, Jie Tang

Tetrahedron 2016 Volume 72(Issue 44) pp:7025-7031

Publication Date(Web):3 November 2016

DOI:10.1016/j.tet.2016.09.039

An efficient method for construction of 3-arylquinolin-4(1H)-ones via in situ Meinwald rearrangement/intramolecular reductive cyclization of 2′-nitrochalcone epoxides has been developed. The practical approach is of excellent functional groups compatibility with as high as 98% yield under mild reaction conditions. Trapping and NMR analysis about the key intermediates of the transformation provided insights to propose a plausible mechanism for the intramolecular reductive cyclization. Moreover, further derivation successfully furnished hydroxyl substituted and N-methyl substituted derivatives which may provide a promising potential application in exploring biologically active compounds of 3-arylquinolin-4(1H)-ones.

Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

Co-reporter:Libo Ruan, Min Shi, Nian Li, Xu Ding, Fan Yang, and Jie Tang

Organic Letters 2014 Volume 16(Issue 3) pp:733-735

Publication Date(Web):January 29, 2014

DOI:10.1021/ol403762e

An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.

A novel efficient protocol for preparation of 3-formyl-2-arylbenzo[b]furan derivatives

Co-reporter:Benren Liao, Libo Ruan, Min Shi, Nian Li, Liang Chang, Leping Liu, Fan Yang, Jie Tang

Tetrahedron Letters 2014 Volume 55(Issue 21) pp:3274-3277

Publication Date(Web):21 May 2014

DOI:10.1016/j.tetlet.2014.04.050

An efficient method for preparation of 3-formyl-2-arylbenzo[b]furan derivatives 4 from 3-chloro-2-(2-methoxyaryl)-1-arylprop-2-en-1-one 2 was developed, and the desired product was obtained in good to excellent yields. By converting 2-(2-methoxyphenyl)-3-oxo-3-phenylpropanal 1 to 2, the regioselectivity problem occurring in the reaction when using 1 as the starting material was successfully avoided. Furthermore, a one-pot procedure for the successive demethylation, cyclization, and hydrolysis was evolved, although the intermediate 3-(dibromomethyl)-2-phenylbenzo[b]furan 3a could be isolated. A plausible mechanism was proposed based on some in situ investigations.

An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

Co-reporter:Libo Ruan, Min Shi, Shiwei Mao, Lifang Yu, Fan Yang, Jie Tang

Tetrahedron 2014 70(5) pp: 1065-1070

Publication Date(Web):

DOI:10.1016/j.tet.2013.12.050

Dearomatization Strategy of β-Enamino Ester: Construction of Indenoazepines via Tandem Michael Addition/Polycyclization

Co-reporter:Min Yang, Jie Tang, and Renhua Fan

Organic Letters 2013 Volume 15(Issue 13) pp:3464-3467

Publication Date(Web):June 24, 2013

DOI:10.1021/ol401553n

A dearomatization strategy of β-enamino esters was developed to construct indenoazepine derivatives. The oxidative dearomatization was combined with a base-promoted tandem Michael addition/polycyclization and an acid-catalyzed aromatization. The nonaromatic structure of the Michael adducts might be essential to the realization of the 7-endo-dig cyclization.

A Tris(bipyridine)ruthenium(II)-Cyclodextrin Derivative: Synthesis, Luminescent Properties, and Application in Electrochemiluminescence DNA Sensors

Co-reporter:Dr. Hong Chen;Dr. Xiuhua Wang;Dr. Yantao Qi;Shanshan Zheng;Qiong Chen; Pingang He;Dr. Fan Zhang; Fan Yang; Jie Tang; Yuzhi Fang

ChemPlusChem 2013 Volume 78( Issue 8) pp:780-784

Publication Date(Web):

DOI:10.1002/cplu.201300071

Accessing N-heteroarylated indoles and benzimidazoles from 2-alkynyl cyclohexadienimines and cyclohexadienones through metal-catalyzed tandem reactions

Co-reporter:Min Yang, Jie Tang and Renhua Fan

Chemical Communications 2012 vol. 48(Issue 96) pp:11775-11777

Publication Date(Web):22 Oct 2012

DOI:10.1039/C2CC36113B

N-Indolyl or N-benzofuranyl indoles and benzimidazoles were prepared through metal-catalyzed tandem reactions between 2-alkynyl cyclohexadienimines or cyclohexadienones and 2-alkynylanilines or N1-benzylbenzene-1,2-diamine.

Synthesis and Biological Evaluation of Heterocyclic Ring-Fused Betulinic Acid Derivatives as Novel Inhibitors of Osteoclast Differentiation and Bone Resorption

Co-reporter:Jun Xu ; Zhenxi Li ; Jian Luo ; Fan Yang ; Ting Liu ; Mingyao Liu ; Wen-Wei Qiu

Journal of Medicinal Chemistry 2012 Volume 55(Issue 7) pp:3122-3134

Publication Date(Web):March 21, 2012

DOI:10.1021/jm201540h

A series of betulinic acid (BA) derivatives were designed and synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects of RANKL-induced osteoclastogenesis were evaluated by using a cell-based tartrate-resistant acid phosphatase (TRAP) activity assay. To our delight, most of these compounds exhibited a dramatic increase in inhibitory potency, compared with BA. The most potent compound, 20, showed 66.9% inhibition even at the low concentration of 0.1 μM, which was about 200-fold more potent than the lead compound BA. What’s more, the cytotoxicity assay on RAW264.7 suggested that the inhibition of 20 on osteoclast differentiation did not result from its cytotoxicity. The primary mechanistic study indicated that 20 could inhibit osteoclastogenesis-related marker gene expression levels of cathepsin K and TRAP. More importantly, 20 could attenuate bone loss of ovariectomy mouse in vivo. Therefore, these BA derivatives could be used as potential leads for the development of a new type of antiosteoporosis agent.

Organic photosensitizers with N-carboxymethyl pyridinium acceptor/anchoring group for dye-sensitized solar cells

Co-reporter:Jia Jin, Yifan Shan, Fan Yang, Hua Lai, Hongwei Tan, Xiaofeng Liu, Jie Tang, Qiang Fang

Synthetic Metals 2012 Volume 162(Issue 24) pp:2222-2227

Publication Date(Web):31 December 2012

DOI:10.1016/j.synthmet.2012.11.001

Four new organic dyes with N-carboxymethyl pyridinium as electron acceptors/anchoring groups were designed and synthesized. The optical and electrochemical properties were characterized by UV–vis, fluorescence spectroscopy and cyclic voltammetry. The absorption spectra of the four pyridinium dyes were in the range of 450–650 nm. The dye with triphenylamine as the electron donor shows a solar-energy-to-electricity conversion efficiency (η) of 2.33% in comparison with the reference Ru-complex (N719 dye) with a η value of 5.45% under the same experimental conditions. The dye with phenoxazine as the electron donor gives broad IPCE spectra in the range of 400–750 nm. All these new dyes are simple in structure, very easy to synthesize, and gives high Voc.Graphical abstractHighlights► Four novel N-carboxymethyl pyridinium dyes were designed and synthesized. ► The new dyes are simple in structure, very easy to synthesize, and gives high Voc. ► CB1 obtained a η value of 2.33% (the reference Ru-complex N719 dye 5.45%).

A novel Friedlander-type synthesis of 3-aryl quinolines from 3-oxo-2,3-diaryl-propionaldehydes

Co-reporter:Wanrong Luo, Qiuchao Mu, Wenwei Qiu, Ting Liu, Fan Yang, Xiaofeng Liu, Jie Tang

Tetrahedron 2011 67(37) pp: 7090-7095

Publication Date(Web):

DOI:10.1016/j.tet.2011.07.004

Synthesis of a β-cyclodextrin derivate and its molecular recognition behavior on modified glassy carbon electrode by diazotization

Co-reporter:Xiuhua Wang, Hao Fan, Fan Zhang, Yantao Qi, Wenwei Qiu, Fan Yang, Jie Tang, Pingang He

Tetrahedron 2010 66(39) pp: 7815-7820

Publication Date(Web):

DOI:10.1016/j.tet.2010.07.052

Pyridinium Conjugated Ferrocenes with Thien and Bithien Bridges: Synthesis and Electrochemical Properties

Co-reporter:Yonghua GONG;Wenwei QIU;Fan YANG;Pierre AUDEBERT;Gilles CLAVIER;Fabien MIOMANDRE

Chinese Journal of Chemistry 2009 Volume 27( Issue 8) pp:1515-1522

Publication Date(Web):

DOI:10.1002/cjoc.200990255

Abstract

Three di- and tri-branched pyridinium salts with ferrocene ends and thienyl or bithienyl bridges, (E,E)-N-methyl-2,4,6-tris{2-[5-(2-ferrocenylvinyl)thien-2-yl]vinyl} pyridinium iodide, (E,E)-N-methyl-2,6-bis- {2-[5′-(2-ferrocenylvinyl)-2,2′-bithien-5-yl]vinyl} pyridinium iodide, and (E,E)-N-methyl-2,4,6-tris-{2-[5′-(2-ferrocenylvinyl)-2,2′-bithien-5-yl]vinyl}pyridinium iodide, were designed and successfully synthesized. The electrochemical properties of these compounds were primarily investigated, showing that most of these multiferrocenyl pyridinium salts are potential electrochemical molecular materials with good oxidation-reduction reversibility.

Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

Co-reporter:Wen-Wei Qiu, Qiang Shen, Fan Yang, Bo Wang, Hui Zou, Jing-Ya Li, Jia Li, Jie Tang

Bioorganic & Medicinal Chemistry Letters 2009 Volume 19(Issue 23) pp:6618-6622

Publication Date(Web):1 December 2009

DOI:10.1016/j.bmcl.2009.10.017

A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 μM) and 29 (IC50 = 0.64 μM) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP.A series of heterocyclic ring-substituted maslinic acid derivatives were prepared and subsequently evaluated on PTP1B, TCPTP and related PTPs in order to increase PTP1B inhibitory activity and especially selectivity for PTP1B over TCPTP.

Imidazolium-modified poly(l-leucine) catalyst: an efficient and recoverable catalyst for Juliá–Colonna reactions

Co-reporter:Wenwei Qiu, Linmei He, Qi Chen, Wanrong Luo, Zhichao Yu, Fan Yang, Jie Tang

Tetrahedron Letters 2009 50(37) pp: 5225-5227

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.06.127

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system

Co-reporter:Bo Wang, Fan Yang, Yi-Fan Shan, Wen-Wei Qiu, Jie Tang

Tetrahedron 2009 65(27) pp: 5409-5412

Publication Date(Web):

DOI:10.1016/j.tet.2009.04.046

A Novel and Efficient Process for Preparation of 2,4-Diphenyl-4-methyl-1-pentene in Brönsted Acidic Ionic Liquid [Hmim]+B

Co-reporter:Zhang Peng-Rong;Du Ji-Yan;Yang Fan;Zou Gang;Tang Jie

Chinese Journal of Chemistry 2005 Volume 23(Issue 5) pp:

Publication Date(Web):14 JUN 2005

DOI:10.1002/cjoc.200590581

Highly selective dimerization of α-methylstyrene (AMS) was effected using a Brönsted acidic ionic liquid, [Hmim]⁺B, as solvent as well as catalyst, providing the industrial high-value olefin, 2,4-diphenyl-4-methyl-1-pentene (1-PT). The desired dimer 1-PT could be obtained in 90% yield at 96% conversion in the dimerization of AMS under optimized conditions. Features of the procedure include use of readily available ionic liquid-catalyst, exclusion of volatile organic solvents, higher selectivity and efficiency for 1-PT.

Immobilization of HX: [Hmim]X as halogenating agent, recyclable catalyst and medium for conversion of alcohols to alkyl halides

Co-reporter:Hai-Hong Wu;Ming-Yuan He;Jing Sun;Fan Yang

Chinese Journal of Chemistry 2004 Volume 22(Issue 7) pp:619-621

Publication Date(Web):26 AUG 2010

DOI:10.1002/cjoc.20040220702

HX is immobilized by reaction of halogen acid with methylimidazole, and the formed ionic liquid [Hmim]X was used as halogenating agent, catalyst as well as medium for conversion of alcohols to alkyl halides. Excellent yields were obtained. The halides produced could be easily separated from the reaction mixture via simple decantation, and the ionic liquid [Hmim]X could be regenerated conveniently by adding equivalent of halogen acids followed by removal of water.

Heck reaction of iodoarenes with methyl acrylate catalyzed by cyclopalladated complexes of tertiary arylamines immobilized in ionic liquid [Bmim]+BF4−

Co-reporter:Rui Zheng;Fan Yang;Gang Zou;Ming-Yuan He

Chinese Journal of Chemistry 2003 Volume 21(Issue 9) pp:

Publication Date(Web):26 AUG 2010

DOI:10.1002/cjoc.20030210902

Heck reaction of iodoarenes with methyl acrylate, catalyzed by cyclopalladated complexes of tertiary arylamines, was investigated in ionic liquid 1-butyl-3-methy Imidazolium tetrafluoroborate ([Bmim] ⁺BF₄⁻). The products can be isolated conveniently from the ionic liquid-catalyst system. The catalysts could be reused for more than 10 times still with satisfactory catalytic activity.

Accessing N-heteroarylated indoles and benzimidazoles from 2-alkynyl cyclohexadienimines and cyclohexadienones through metal-catalyzed tandem reactions

Co-reporter:Min Yang, Jie Tang and Renhua Fan

Chemical Communications 2012 - vol. 48(Issue 96) pp:NaN11777-11777

Publication Date(Web):2012/10/22

DOI:10.1039/C2CC36113B