Xin-Ping Hui

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Name: 惠新平; Hui, XinPing

Organization: Lanzhou University , China

Department: State Key Laboratory of Applied Organic Chemistry

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Highly Stereoselective Synthesis of Functionalized Pyrrolo[3,2-c]quinolines via N-Heterocyclic Carbene Catalyzed Cascade Sequence

Co-reporter:Yu-Jie Yang, Hai-Rui Zhang, Shi-Ya Zhu, Ping Zhu, and Xin-Ping Hui

Organic Letters 2014 Volume 16(Issue 19) pp:5048-5051

Publication Date(Web):September 23, 2014

DOI:10.1021/ol5023917

An N-heterocyclic carbene-catalyzed stereoselective Michael–Mannich–lactamization cascade reaction of tosyl-protected o-amino aromatic aldimines and 2-bromoenals for the construction of functionalized pyrrolo[3,2-c]quinolines with three consecutive stereocenters was achieved in good yields with excellent diastereo- and enantioselectivities.

Fabrication of magnetic amino-functionalized nanoparticles for S-arylation of heterocyclic thiols

Co-reporter:Yanhong Liu, Lincheng Zhou, Xinping Hui, Zhenwen Dong, Hao Zhu, Yanming Shao and Yanfeng Li

RSC Advances 2014 vol. 4(Issue 90) pp:48980-48985

Publication Date(Web):19 Sep 2014

DOI:10.1039/C4RA08782H

A series of uniformed mono-disperse magnetic nanoligands (MNLs) (CoFe2O4–NH2 (MNL A), Fe3O4@Si(CH2)3NH2 (MNL B), Fe3O4@Si(CH2)3NHC(O) (CH2)2PEI (MNL C) and Fe3O4@Si(CH2)3NHC(O)PEI (MNL D)) were obtained by loading two ligands, an aminosilane coupling agent and PEI-600, onto magnetic nanoparticles prepared using a solvothermal method. The catalytic applications of the synthesized MNLs were explored for the cross-coupling reaction of heterocyclic thiols with aromatic iodides. The reactions were carried out in the presence of CuI (5 mol%), MNL (10 mol% N) and K2CO3 (1.3 eq.) in DMF at 120 °C. A variety of heterocyclic sulfides were afforded in good to excellent yields (up to 98%) when MNL B was used. The magnetic, crystal, organic matter structure and morphology of MNL B exhibited no obvious changes after five consecutive cycles. XPS characterization of MNL B revealed the combination of a small amount of Cu0 nanoparticles, but this had no significant effect on catalytic performance.

Tandem Aza-MichaelAldol Reactions: One-Pot Synthesis of Functionalized Piperidine Derivatives

Co-reporter:Fu-Ping Huang;Zhen-Wen Dong;Hai-Rui Zhang

Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 2) pp:532-538

Publication Date(Web):

DOI:10.1002/jhet.1750

A series of novel functionalized piperidine derivatives were conveniently prepared by three-component tandem aza-Michael–Aldol reactions of α,β-unsaturated enones with substituted sulfonamides in the presence of DBU. The structures of the compounds synthesized were characterized by spectral data and X-ray crystal diffraction.

N-Heterocyclic Carbene-Catalyzed Stereoselective Cascade Reaction: Synthesis of Functionalized Tetrahydroquinolines

Co-reporter:Hai-Rui Zhang, Zhen-Wen Dong, Yu-Jie Yang, Ping-Luan Wang, and Xin-Ping Hui

Organic Letters 2013 Volume 15(Issue 18) pp:4750-4753

Publication Date(Web):September 10, 2013

DOI:10.1021/ol4024985

The first N-heterocyclic carbene-catalyzed stereoselective aza-Michael–Michael–lactonization cascade reaction of 2′-aminophenylenones and 2-bromoenals for the construction of chiral functionalized tetrahydroquinolines with three consecutive stereogenic centers has been achieved in high yields (up to 98%) with excellent diastereo- (>25:1) and enantioselectivities (up to 98.7% ee).

Brnsted Acid-Catalyzed Four-Component Cascade Reaction: Facile Synthesis of Hexahydroimidazo[1,2-a]pyridines

Co-reporter:Ren-Lin Wang;Ping Zhu;Yu Lu;Fu-Ping Huang

Advanced Synthesis & Catalysis 2013 Volume 355( Issue 1) pp:87-92

Publication Date(Web):

DOI:10.1002/adsc.201200145

Abstract

An efficient four-component cascade reaction for the synthesis of trisubstituted hexahydroimidazo[1,2-a]pyridines starting from readily available aldehydes, ketones and ethane-1,2-diamine catalyzed by p-toluenesulfonic acid is described. Two new cycles and five new bonds are constructed with all reactants being efficiently utilized in this transformation. The mechanism of the reaction was investigated and some crucial reaction intermediates were observed.

Synergistic Chiral Ion Pair Catalysts for Asymmetric Catalytic Synthesis of Quaternary α,β-Diamino Acids

Co-reporter:Shi-Hui Shi, Fu-Ping Huang, Ping Zhu, Zhen-Wen Dong, and Xin-Ping Hui

Organic Letters 2012 Volume 14(Issue 8) pp:2010-2013

Publication Date(Web):April 3, 2012

DOI:10.1021/ol300510b

The combination of a chiral phosphate anion with a silver ion has been demonstrated as a powerful and synergistic ion pair catalyst for the aza-Mannich reaction. A series of valuable quaternary α,β-diamino acid derivatives was obtained in high yield, and with excellent diastereo- (up to 25:1 dr) and enantioselectivity (up to 99% ee). The adducts can be smoothly transformed into the corresponding protected chiral quaternary α,β-diamino acids by a one-pot hydrolysis reaction.

Conjugation of substituted ferrocenyl to thiadiazine as apoptosis-inducing agents targeting the Bax/Bcl-2 pathway

Co-reporter:Ruidong Miao, Juan Wei, Minghua Lv, Yan Cai, Yuping Du, Xinping Hui, Qin Wang

European Journal of Medicinal Chemistry 2011 Volume 46(Issue 10) pp:5000-5009

Publication Date(Web):October 2011

DOI:10.1016/j.ejmech.2011.08.007

Ferrocene compounds are a class of biologically active compounds that has antitumour and antifungal properties. This study investigated the induction of apoptosis in human fibrosarcoma cells (HT1080) after treatment with a series of 6-ferrocenyl-3-subsituted7H-1,2,4-triazolo[3,4-b]- 1,3,4-thiadiazine (FTFs). We found that FTFs could suppress the viability of HT1080 cells. Cell cycle analysis showed that proliferative inhibition of HT1080 cells occurred through apoptosis, as the cells were blocked in G1 phase. Moreover, mitochondrial membrane staining assay demonstrated that FTFs exposure significantly decreased mitochondrial membrane potential. Finally, under the stress of FTFs, Bax/Bcl-2 ratio in HT1080 cells was significantly increased. These results suggested that FTFs-induced apoptosis in HT1080 cells may work dependent on a Bax/Bcl-2 pathway.The cyclization of 4-amino-5-substituted 1,2,4-triazol-3-thione with α-halogenocarbonyl compounds has been the most useful method for the formation of the 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine ring system. Highlights► Thiadiazine derivatives could suppress the viability of HT1080 cells. ► Proliferative inhibition of HT1080 cells occurred through apoptosis. ► Thiadiazine derivatives exposure decreased mitochondrial membrane potential. ► Bax/Bcl-2 ratio in cells was increased under the stress of Thiadiazine derivatives.

N-Heterocyclic Carbene-Catalyzed Oxidative Esterification Reaction of Aldehydes with Alkyl Halides under Aerobic Conditions

Co-reporter:Yang-Chun Xin;Shi-Hui Shi;Dong-Dong Xie, ;Peng-Fei Xu

European Journal of Organic Chemistry 2011 Volume 2011( Issue 32) pp:6527-6531

Publication Date(Web):

DOI:10.1002/ejoc.201100937

Abstract

An efficient N-heterocyclic carbene-catalyzed oxidative esterification reaction of aldehydes with alkyl halides or alkyl 4-methylbenzenesulfonate is reported. It was worth noting that (1) the configuration of alkyl halides or alkyl 4-methylbenzenesulfonates was inverted completely, and (2) the presence of oxygen was crucial for this transformation. The reaction proceeded smoothly under mild conditions and various esters were afforded in moderate to good yields. In addition, we have developed an efficient tandem oxidation/esterification reaction of alcohols. This methodology provides a rare example of a reaction of the Breslow intermediate to sp³-carbon centered electrophiles.

Efficient copper-catalyzed C–S cross-coupling of heterocyclic thiols with aryl iodides

Co-reporter:Liang-Feng Niu, Yan Cai, Chao Liang, Xin-Ping Hui, Peng-Fei Xu

Tetrahedron 2011 67(16) pp: 2878-2881

Publication Date(Web):

DOI:10.1016/j.tet.2011.02.064

Enantioselective addition of phenylacetylene to aldehydes catalyzed by polymer-supported titanium(IV) complexes of -hydroxy amides

Co-reporter:Xin-Ping Hui;Lu-Ning Huang;Ya-Min Li;Ren-Lin Wang ;Peng-Fei Xu

Chirality 2010 Volume 22( Issue 3) pp:347-354

Publication Date(Web):

DOI:10.1002/chir.20749

Abstract

A series of polymer-supported chiral β-hydroxy amides and C₂-symmetric β-hydroxy amides have been synthesized and successfully used for the enantioselective addition of phenylacetylene to aldehydes. High yields (up to 93%) and enantioselectivities (up to 92% ee) were achieved by using polymer-supported chiral β-hydroxy amide 4b. The resin 4b is reused four times, giving the product with enantioselectivity 80% ee. Fortunately, it is found that this heterogonous system is suitable not only for aromatic aldehydes but also aliphatic aldehyde. Chirality, 2010. © 2009 Wiley-Liss, Inc.

Synthesis of new β-hydroxy amide ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aliphatic and vinyl aldehydes

Co-reporter:Ya-Min Li, Yi-Quan Tang, Xin-Ping Hui, Lu-Ning Huang, Peng-Fei Xu

Tetrahedron 2009 65(18) pp: 3611-3614

Publication Date(Web):

DOI:10.1016/j.tet.2009.03.005

Highly enantioselective addition of methyl propiolate to aldehydes catalyzed by a titanium(IV) complex of a β-hydroxy amide

Co-reporter:Tao Xu, Chao Liang, Yan Cai, Jian Li, Ya-Min Li, Xin-Ping Hui

Tetrahedron: Asymmetry 2009 Volume 20(Issue 23) pp:2733-2736

Publication Date(Web):11 December 2009

DOI:10.1016/j.tetasy.2009.11.022