Liping Song

Find an error

Name: 宋力平; LiPing Song

Organization: Shanghai University , China

Department: Department of Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Unexpected straightforward formation of trifluoromethylated pyrido[2,3-d]pyrimidine derivatives via one-pot, MCRs

Co-reporter:Yang Wang, Lu Zhou, Yingjun Zhu, Min Zhang, Liping Song, Hongmei Deng

Journal of Fluorine Chemistry 2017 Volume 200(Volume 200) pp:

Publication Date(Web):1 August 2017

DOI:10.1016/j.jfluchem.2017.06.016

•MCRs synthesis of trifluoromethylated pyrido[2,3-d]pyrimidines.•Straightforward formation of aromatized products.•Spontaneous dehydration of α-CF3 hemi-aminals without dehydrating reagents.•A more consecutive approach was achieved.An efficient synthesis of trifluoromethylated pyrido[2,3-d]pyrimidine derivatives was achieved via tandem Knoevenagel–Michael addition of 6-aminopyrimidine-2,4(1H,3H)-dione (1), aryldehyde (2) and ethyl 4,4,4-trifluoro-3-oxobutanoate (3) in refluxed DMSO in the presence of 25 mol% of piperidine as a catalyst. Compared with the stability of α-trifluoromethylated hemi-aminal or himi-ketal moiety, this protocol straightforwardly afforded the unexpected aromatized compounds via a spontaneous dehydration, followed by an auto-oxidation under the present reaction conditions. The structures of new compounds were determined by spectroscopic methods In addition, a possible mechanism for the formation of compound 4 was presented.A facile and consecutive one-pot three-component reaction for straightforward preparation of unexpected aromatized trifluoromethylated pyrido[2,3-d]pyrimidine derivatives is described.Download high-res image (132KB)Download full-size image

Di- and Tetranuclear Palladium(II) Complexes Containing C,N-Bidentate Furoylhydrazone for Suzuki–Miyaura Reactions

Co-reporter:Hengyu Qian;Tongyan Zhang;Shuyan Yu;Qi Yuan;Luyan Sun;Dengfeng Zhang;Zhigang Yin;Yongxia Dai

European Journal of Organic Chemistry 2017 Volume 2017(Issue 10) pp:1337-1342

Publication Date(Web):2017/03/10

DOI:10.1002/ejoc.201700027

Furoylhydrazones of general formula 4-R–C6H4–CH=NNH–CO–2-C4H3O [R = H (HL1) and OCH3 (HL2)] have been conveniently prepared from furan-2-carbohydrazide. The reaction of HL1 with Li2[PdCl4] and CH3COONa provided the di-µ-chloro-bridged cyclopalladated complex [Pd(C6H4–CH=N–NH–CO–2-C4H3O)(µ-Cl)]2 (1) through aryl C–H bond activation, whereas the unusual tetranuclear cluster [Pd(4-CH3O–C6H4–CH=N–NH–CO–2-C4H3O)(µ-Cl)]4 (2) was obtained from the reaction with ligand HL2. The crystal structures of 1 and 2 show a slightly distorted square-planar coordination geometry around the palladium ion to which the furoylhydrazone is attached in a bidentate fashion. The two palladium(II) complexes were able to catalyze the Suzuki–Miyaura coupling reactions of phenylboronic acid with aryl halides to afford the desired biaryl derivatives in excellent yields (up to 99.2 %).

A facile and consecutive approach to trifluoromethylated spirochromeno[2,3-c]-6H-Pyrazol-2′,5-dione derivatives

Co-reporter:Zhangping Kang, Yang Wang, Lu Zhou, Min Zhang, Liping Song, Hongmei Deng

Journal of Fluorine Chemistry 2016 Volume 188() pp:131-138

Publication Date(Web):August 2016

DOI:10.1016/j.jfluchem.2016.06.020

•MCRs synthesis of trifluoromethylated spiroheterocycles was described.•A more consecutive approach was achieved.•The p-TSA played dual roles in the conversion.•A plausible reaction mechanism was proposed.A facile and consecutive one-pot, multi-component reaction for synthesis of trifluoromethylated spirochromeno[2,3-c]-6H-pyrazol-2′,5-dione derivatives by the reaction of isatin, cyclohexane-1,3-dione and 1-aryl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one in the presence of p- toluenesulfonic acid (p-TSA) with good yields was reported. Compared with the stepwise reactions, the p-TSA played dual roles as both catalyst and dehydrating agent in the conversion. The structures of new compounds were determined by spectroscopic methods and X-ray diffraction analysis. In addition, a possible mechanism for the formation of compound 5 was presented.A facile and consecutive one-pot three-component reaction for preparation of trifluoromethylated spirochromeno[2,3-c]−6H-pyrazol-2′,5-dione derivatives in the presence of p-TSA is described.

Convenient one-pot synthesis of monofluorinated functionalized 4-H-pyran derivatives via multi-component reactions

Co-reporter:Xiaoling Xu, Wei Shi, Yu Zhou, Yang Wang, Min Zhang, Liping Song, Hongmei Deng

Journal of Fluorine Chemistry 2015 Volume 176() pp:127-133

Publication Date(Web):August 2015

DOI:10.1016/j.jfluchem.2015.05.008

•This manuscript reports the study of one-pot, multi-component reaction catalyzed by NaOH.•The new fluorinated building-block strategy toward pharmacologically relevant monofluorinated 4-H-pyrans.•The solvent ethanol plays dual roles as both reactant and reaction medium.•The possible reaction mechanism is discussed on the basis of two supporting experiments.A series of functionalized 3-fluoro-2,3-dihydro-4H-pyran derivatives were efficiently synthesized from ethyl 2-fluoroacetoacetate 1, malononitrile 2 and aromatic aldehydes 3via one-pot, multi-component reactions catalyzed by NaOH. The solvent ethanol played dual roles as both reactant and reaction medium, resulting in the further occurrence of intramolecular cyclization to afford cyclic products 4. The structures of product 4 were determined by spectral methods and X-ray diffraction analysis. A possible reaction mechanism for the formation of 4 was presented on the basis of two supporting experiments.A convenient method for synthesis of monofluorinated functionalized 4-H-pyran derivatives from readily available starting materials via one-pot, multi-component reaction catalyzed by NaOH is described.

First synthesis of unexpected functionalized trifluoromethylated 8-oxa-2,4-diazaspiro[5.5]undecanes via one-pot MCRs

Co-reporter:Jia Li, Wei Shi, WenXin Yang, ZhangPing Kang, Min Zhang and LiPing Song

RSC Advances 2014 vol. 4(Issue 56) pp:29549-29554

Publication Date(Web):11 Jun 2014

DOI:10.1039/C4RA03199G

Ethyl-7,11-diaryl-9-hydroxy-1,3,5-trioxo-9-(trifluoromethyl)-8-oxa-2,4-diazaspiro[5.5]undecane-10-carboxylate derivatives (4) were synthesized from barbituric acid, aromatic aldehydes and ethyl 4,4,4-trifluoro-3-oxobutanoate via a one-pot, multi-component reaction catalyzed by Et3N. The effect of catalyst and temperature on reaction efficiency and yield was investigated. In addition, the treatment of 4 with SOCl2/pyridine in the solvent CH3CN afforded the corresponding dehydrated products 5. A plausible reaction mechanism for the formation of compounds 4 was presented.

Regioselective Synthesis of 2,6-Dimethyl-3,5-bis[(3-aryl-5-trifluoromethyl)-isoxazol-4-carbonyl]-pyridine Derivatives

Co-reporter:Yindi Yang;Min Zhang;Yiwen Zhu;Li Zhang;Qiqiang Xie;Hongmei Deng

Chinese Journal of Chemistry 2013 Volume 31( Issue 7) pp:950-954

Publication Date(Web):

DOI:10.1002/cjoc.201300366

Abstract

Ethyl 4,4,4-trifluoro-3-oxo-butyrate reacted with 2,6-dimethyl-3,5-diacetyl-pyridine 1 in the presence of NaOC₂H₅ at 0°C to give 2,6-dimethyl-3,5-bis(4,4,4-trifluoro-1,3-oxo-butyl)-pyridine (2a) in good yield. Cyclization reaction of 2a and aryl imidoyl chlorides 5a–5i, obtained from chlorination of aryl oximes with N-chlorosuccimide, afforded 2,6-dimethyl-3,5-bis[(3-aryl-5-trifluoromethyl)-isoxazol-4-carbonyl]-pyridine derivatives 6a–6i.

A facile and convenient way to functionalized trifluoromethylated spirocyclic[indole-3,4-pyrano[2,3-c]pyrazole] derivatives

Co-reporter:Xiaoqing Liu, Xiaoling Xu, Xu Wang, Wenxin Yang, Qun Qian, Min Zhang, Liping Song, Hongmei Deng, Min Shao

Tetrahedron Letters 2013 Volume 54(Issue 33) pp:4451-4455

Publication Date(Web):14 August 2013

DOI:10.1016/j.tetlet.2013.06.038

An efficient and consecutive one-pot, two-step, four-component reaction for the synthesis of trifluoromethylated spirocyclic[indole-3,4-pyrano[2,3-c]pyrazole] derivatives by the reaction of isatin, malononitrile, ethyl cyanoacetate, or cyanoacetamide, ethyl 4,4,4-trifluoroacetoacetate and hydrazine in the presence of a catalytic amount of piperidine in good yields was described. The structures of new compounds were determined by spectroscopic methods, microanalysis, and X-ray diffraction analysis. In addition, a possible mechanism of the reaction was proposed herein.

Iodine catalyzed one-pot multi-component reaction to CF3-containing spiro[indene-2,3′-piperidine] derivatives

Co-reporter:Baifan Dai, Yijun Duan, Xiaoqing Liu, Liping Song, Min Zhang, Weiguo Cao, Shizheng Zhu, Hongmei Deng, Min Shao

Journal of Fluorine Chemistry 2012 Volume 133() pp:127-133

Publication Date(Web):January 2012

DOI:10.1016/j.jfluchem.2011.09.006

In the presence of a catalytic amount of molecular iodine (0.1 equiv.), the one-pot multi-component reaction of ethyl trifluoroacetoacetate 1, indan-1,3-dione 2, ammonium acetate 3 and aromatic aldehyde 4 mainly gave the ethyl-6′-hydroxy-1,3-dioxo-2′,4′-diaryl-6′-(trifluoromethyl)-1,3-dihydrospiro[indene-2,3′-piperidine]-5′-carboxylate derivatives 5, along with the minor product 2-trifluoromethyl-2,3,4,5-tetrahydro-1H-indeno[1,2-b]pyridine derivatives 6. A plausible reaction mechanism for the formation of 5, 6 was presented. The structures of compounds 5, 6 were fully confirmed by 1H NMR, 19F NMR, MS, IR spectroscopies and elemental analysis or high resolution mass spectra (HRMS). Meanwhile, the representative 5a and 6h were further confirmed by XRD analysis.Graphical abstractHighlights► The manuscript reports the study of one-pot, four-component reaction catalyzed by iodine. ► The unexpected formation was attributed to the unique catalytic activity of iodine. ► The influence of the reaction and the scope and limitation were studied. ► The new fluorinated building-block strategy towards CF3-containing spiroheterocycles.

Facile one-pot three-component reaction to synthesize trifluoromethylated cyclopenta[b]pyran derivatives and their further transformation

Co-reporter:Jianning Liu, Jia Li, Li Zhang, Liping Song, Min Zhang, Weiguo Cao, Shizheng Zhu, Hongmei Deng, Min Shao

Tetrahedron Letters 2012 Volume 53(Issue 19) pp:2469-2472

Publication Date(Web):9 May 2012

DOI:10.1016/j.tetlet.2012.03.023

A series of trifluoromethylated cyclopenta[b]pyran derivatives were synthesized efficiently from 1,3-cyclopentanedione, arylaldehydes, and ethyl 4,4,4-trifluoro-3-oxobutanoate via one-pot multi-component reaction catalyzed by NH4OAc. This one-pot multi-component process comprises an initial Michael addition and a subsequent intramolecular cyclization reaction. The effect of catalysts and solvents on the reaction efficiency and the yield were investigated. The structure of product 4f was further confirmed by XRD analysis. Meanwhile, further transformation of hemi-ketal moiety to the corresponding dehydrated product is also studied. In addition, a possible mechanism of this reaction is proposed herein.

Convenient Synthesis of 3,5-Biscarbamoyl-pyridine Derivatives

Co-reporter:Xiayun Wang;Yiwen Zhu;Min Zhang;Dongliang Lu;Qun Qian;Yali Chen;Weiguo Cao;Hongmei Deng

Chinese Journal of Chemistry 2011 Volume 29( Issue 10) pp:2119-2123

Publication Date(Web):

DOI:10.1002/cjoc.201180367

Abstract

An efficient and convenient method for synthesis of 3,5-bis-carbamoyl-2,6-dimethylpyridine derivatives was achieved in good to excellent yields by reaction of anilines with 3,5-bis(3′,5′-dimethyl-1′-pyrazolyl-carbonyl)-2,6-dimethylpyridine, in which pyrazoles served as leaving groups. The structures of products were confirmed by spectra data and microanalysis.

First synthesis of 3-aryl-4-unsubstituted-6-CF3-pyridin-2-ones via aryl migration reaction in the presence of PhI(OAc)2/NaOH

Co-reporter:Hai Yi, Liping Song, Wei Wang, Jianning Liu, Shizheng Zhu, Hongmei Deng and Min Shao

Chemical Communications 2010 vol. 46(Issue 37) pp:6941-6943

Publication Date(Web):23 Aug 2010

DOI:10.1039/C0CC01815E

3-Aryl-4-unsubstituted-6-CF3-pyridin-2-ones have been efficiently synthesized from readily available 4-aryl-3-carbamoyl-6-CF3-pyridin-2(1H)-ones by treatment with PhI(OAc)2 in the presence of NaOH.

Convenient one-pot synthesis of fluorinated DHPs derivatives and their further transformations

Co-reporter:Pengyuan Wang, Liping Song, Hai Yi, Min Zhang, Shizheng Zhu, Hongmei Deng, Min Shao

Tetrahedron Letters 2010 Volume 51(Issue 30) pp:3975-3977

Publication Date(Web):28 July 2010

DOI:10.1016/j.tetlet.2010.05.110

One-pot four-component reactions of aromatic aldehyde, Meldrum’s acid, ethyl-4,4,4-trifluoro-1,3-dioxobutanoate, and ammonium acetate afford ethyl 2-hydroxy-6-oxo-4-aryl-2-(trifluoromethyl)piperidine-3-carboxylate in good yields. The one-pot four-component process consists of an initial Michael addition, and a subsequent intramolecular cyclization. The effect of solvents on the reaction efficiency and yield is briefly investigated. The structure of product is further confirmed by XRD analysis. Meanwhile, the further transformation of hemi-aminal moiety to the corresponding dehydrated product is also achieved under the mild reaction conditions. The possible mechanism for the formation of product is presented.An efficient and convenient one-pot four-component synthesis of fluorinated DHPs in good yields is described. The key step involves a tandem Michael addition-intramolecular cyclization process from easily available starting materials.

Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

Co-reporter:Jun Zhang, Min Zhang, Weiguo Cao, Liping Song, Qun Qian, Jiwen Tan, Min Shao

Journal of Fluorine Chemistry 2009 Volume 130(Issue 5) pp:488-492

Publication Date(Web):May 2009

DOI:10.1016/j.jfluchem.2009.02.016

l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines provide a novel method for preparation of ethyl-6-(arylamino)-2-hydroxy-4-phenyl-2-(trifluoromethyl)tetrahydro-2H-pyran-3-carboxylate derivatives in good yields. The reaction was conducted by initial Michael addition, followed by intra-molecular cyclization under mild conditions. The structure of a typical ethyl-2-hydroxy-4-phenyl-6-(m-tolylamino)-2-(trifluoromethyl)tetrahydro-2H-pyran-3-carboxylate (4h) was confirmed by XRD analysis. A plausible mechanism is presented.l-Proline-catalyzed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines provides a novel method for preparation of 2-trifluoromethyl-tetrahydro-pyran derivatives in good yields.

Synthesis of novel substituted pyridine derivatives from 3,5-diacetyl-2,6-dimethylpyridine

Co-reporter:Jun Zhang;Min Zhang;Weiguo Cao;Qun Qian;Jiwen Tan

Heteroatom Chemistry 2009 Volume 20( Issue 3) pp:123-130

Publication Date(Web):

DOI:10.1002/hc.20522

Abstract

A series of novel (1-acetyl-5-aryl-4,5-dihydro)-1H-pyrazole substituted pyridine derivatives and poly substituted [2,3′-bipyridine]-5-carbonitrile derivatives were synthesized from 3,5-diacetyl-2,6-dimethylpyridine. The structures of two typical 3,5-bis[1-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethylpyridines [3b(1) and 3b(2)] were confirmed by X-ray diffraction analysis. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:123–130, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20522

First synthesis of 3-aryl-4-unsubstituted-6-CF3-pyridin-2-ones via aryl migration reaction in the presence of PhI(OAc)2/NaOH

Co-reporter:Hai Yi, Liping Song, Wei Wang, Jianning Liu, Shizheng Zhu, Hongmei Deng and Min Shao

Chemical Communications 2010 - vol. 46(Issue 37) pp:NaN6943-6943

Publication Date(Web):2010/08/23

DOI:10.1039/C0CC01815E

3-Aryl-4-unsubstituted-6-CF3-pyridin-2-ones have been efficiently synthesized from readily available 4-aryl-3-carbamoyl-6-CF3-pyridin-2(1H)-ones by treatment with PhI(OAc)2 in the presence of NaOH.