Co-reporter:Xiao-Jun Liu;Wen-Peng Wang;Cong-De Huo;Zheng-Jun Quan
Catalysis Science & Technology (2011-Present) 2017 vol. 7(Issue 3) pp:565-569
Publication Date(Web):2017/02/07
DOI:10.1039/C6CY02038K
An efficient and general method for Pd-catalyzed dehydrogenative aromatization of dihydro-heteroatom compounds without external O2 and H2 is first described. The protocol firstly uses isoprene as a hydrogen acceptor. Various dihydro-heterocycles including dihydropyrimidinones, dihydropyrimidines and dihydropyridines can be dehydrogenated to produce the corresponding aromatic heterocyclic compounds.
Co-reporter:Zhang Zhang, Shi-Hong Lu, Bin Xu, Xi-Cun Wang
Chinese Chemical Letters 2017 Volume 28, Issue 5(Volume 28, Issue 5) pp:
Publication Date(Web):1 May 2017
DOI:10.1016/j.cclet.2016.12.034
A novel and general carbon-nitrogen and carbon-carbon cross-coupling reaction between 3,4-dihydropyrimidine-2-thiones and copper(I) carboxylates were performed in the presence of palladium acetate. The copper(I) carboxylates act not only as desulfurative reagents but also as sources of carbon nucleophiles. A wide array of highly substituted and functionalized pyrimidines scaffolds were synthesized in good yields.Download high-res image (83KB)Download full-size imageA novel and general carbon-nitrogen and carbon-carbon cross-coupling reaction between dihydropyrimidinthiones and copper(I) carboxylates protocol was performed in the presence of palladium acetate. The copper(I) carboxylates act not only as desulfurative reagents but also as sources of carbon nucleophiles.
Co-reporter:Chunyu Gong;Congde Huo;Xicun Wang;Zhengjun Quan
Chinese Journal of Chemistry 2017 Volume 35(Issue 9) pp:1337-1337
Publication Date(Web):2017/09/01
DOI:10.1002/cjoc.201770091
The cover picture shows a new protocol for the NiCl2-catalyzed cross-electrophile coupling of aryl bromides with pyrimidin-2-yl tosylates to give the corresponding C2-arylation pyrimidine derivatives. This study provides an improvement over previous methods by using pyrimidin-2-yl tosylates instead of halides as coupling partners that are stable and easily available. More details are discussed in the article by Wang et al. on page 1366–1370.
Co-reporter:Chunyu Gong;Congde Huo;Xicun Wang;Zhengjun Quan
Chinese Journal of Chemistry 2017 Volume 35(Issue 9) pp:1366-1370
Publication Date(Web):2017/09/01
DOI:10.1002/cjoc.201700071
A new protocol for the NiCl2-catalyzed cross-electrophile coupling of aryl bromides with pyrimidin-2-yl tosylates to give the corresponding C2-arylation pyrimidine derivatives has been developed. This study provides an improvement over previous methods by using pyrimidin-2-yl tosylates instead of halides as coupling partners that are stable and easily available.
Co-reporter:Yong-Hui Wu;Zhi-Feng Li;Wen-Peng Wang;Zheng-Jun Quan
European Journal of Organic Chemistry 2017 Volume 2017(Issue 37) pp:5546-5553
Publication Date(Web):2017/10/10
DOI:10.1002/ejoc.201700867
The reaction of the 2-phosphaethynolate anion and primary amines for the mechanochemical synthesis of phosphinecarboxamides was studied. The reaction has its own merits, such as rapid reaction rate, high yield, mild and acid-free conditions. The mechanochemical strategy offers a solvent-free reaction environment with real-time monitoring of the parameters, optimizing the reaction conditions and studying the mechanism without requiring further workup. The mechanism was investigated with use of IR, 13C NMR, and 31P NMR spectroscopy.
Co-reporter:Kai-Jie Wei, Zheng-jun Quan, Zhang Zhang, Yu-xia Da and Xi-cun Wang
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 8) pp:2395-2398
Publication Date(Web):25 Jan 2016
DOI:10.1039/C5OB02535D
The copper(I)-promoted cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with aromatic amines and aliphatic amines to deliver C–N coupling products in moderate to good yields is reported in this paper. Central to this strategy is the conversion of disulfides into aryl- and alkyl amines by a copper-promoted chemoselective C–S bond cleavage.
Co-reporter:Zheng-Jun Quan
The Chemical Record 2016 Volume 16( Issue 1) pp:435-444
Publication Date(Web):
DOI:10.1002/tcr.201500212
Abstract
The allylamine skeleton represents a significant class of biologically active nitrogen compounds that are found in various natural products and drugs with well-recognized pharmacological properties. In this personal account, we will briefly discuss the synthesis of allylamine skeletons. We will focus on showing a general protocol for Lewis acid-catalyzed N-allylation of electron-poor N-heterocyclic amides and sulfonamide via an amide-aldehyde-alkene condensation reaction. The substrate scope with respect to N-heterocyclic amides, aldehydes, and alkenes will be discussed. This method is also capable of preparing the Naftifine motif from N-methyl-1-naphthamide or methyl (naphthalene-1-ylmethyl)carbamate, with paraformaldehyde and styrene in a one-pot manner.
Co-reporter:Hai-Peng Gong, Zheng-Jun Quan, Xi-Cun Wang
Tetrahedron 2016 Volume 72(Issue 16) pp:2018-2025
Publication Date(Web):21 April 2016
DOI:10.1016/j.tet.2016.02.069
Pyrimidin-2-yl tosylates which are successfully applied as the electrophiles instead of halides coupled with olefins via Pd(PPh3)2Cl2 catalyzed Mizoroki–Heck reaction conditions to give the corresponding C2-alkenyl pyrimidine derivatives with high β-regioselectivity. This protocol proves to be tolerant of various pyrimidin-2-yl tosylates as well as various olefins including styrene derivatives, aliphatic olefins (vinyl cyanide, methyl acrylate, ethyl acrylate, n-butyl acrylate, butyl vinyl ether, 1-hexene and 1-octene).
Co-reporter:Quanlu Yang, Zhengjun Quan, Baoxin Du, Shang Wu, Peidong Li, Yanxia Sun, Ziqiang Lei and Xicun Wang
Catalysis Science & Technology 2015 vol. 5(Issue 9) pp:4522-4531
Publication Date(Web):10 Jul 2015
DOI:10.1039/C5CY00802F
A biomacromolecule-anchored palladium complex, wool-Pd(OAc)2, was prepared and characterized by IR, XPS, SEM and ICP. The new complex was used as a catalyst for the Liebeskind–Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and aryl boronic acids. Products were isolated in moderate to excellent yields. When 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable of being reused for at least nine rounds, with durable performance and wide substrate tolerance.
Co-reporter:Quan-Lu Yang, Zheng-Jun Quan, Bao-Xin Du, Shang Wu, Yin-Pan Zhang, Pei-Dong Li, Ming-Ming Wang, Zi-Qiang Lei and Xi-Cun Wang
RSC Advances 2015 vol. 5(Issue 73) pp:59770-59779
Publication Date(Web):24 Jun 2015
DOI:10.1039/C5RA09765G
A well-defined heterogeneous palladium catalyst, supported on biomacromolecule, natural wool fibre, was found to be an effective catalyst for the C–C/C–N coupling of pyrimidin-2-yl sulfonates with arylboronic acids, terminal alkynes or anilines, giving the desired coupling products in good to high yields. The catalyst was characterized by XPS, IR, SEM and ICP. More importantly, the easy experimental handling catalyst is stable, shows negligible metal leaching, and can be reused for at least 10 successive runs. Undoubtedly, a wide scope of reactant, insensitive to the electron effects and the excellent coupling yields make these catalyst systems potentially useful in organic synthesis.
Co-reporter:Shuai Sun, Zhengjun Quan and Xicun Wang
RSC Advances 2015 vol. 5(Issue 103) pp:84574-84577
Publication Date(Web):30 Sep 2015
DOI:10.1039/C5RA17731F
Ni(acac)2 and PMHS were found to be an excellent catalytic system for the chemoselective transfer hydrogenation of nitro-compounds to primary amines. Under mild conditions a series of nitro-compounds containing a variety of sensitive functional groups including aldehydes, esters, cyano, and nitrine were reduced to their corresponding amines in good to excellent yields with no byproduct.
Co-reporter:Xu Chen;Zheng-Jun Quan
Applied Organometallic Chemistry 2015 Volume 29( Issue 5) pp:296-300
Publication Date(Web):
DOI:10.1002/aoc.3289
An Fe(III)-catalyzed cross-coupling of N-heteroaromatic tosylates with aryl and alkyl Grignard reagents is presented. The reaction proceeds at −20°C to room temperature with short reaction time (15–30 min.), and the corresponding products are obtained with moderate to high yields. In particular, low-cost and abundantly available FeCl3 or Fe(acetylacetonate)3 catalyze the reaction without other special ligands. All tested N-heteroaromatic tosylates that are available including pyridine and pyrimidine derivatives were subject to the reaction, resulting in the expected products. Copyright © 2015 John Wiley & Sons, Ltd.
Co-reporter:Jun-Ke Wang, Ying-Xiao Zong, Xi-Cun Wang, Yu-Lai Hu, Guo-Ren Yue
Chinese Chemical Letters 2015 Volume 26(Issue 11) pp:1376-1380
Publication Date(Web):November 2015
DOI:10.1016/j.cclet.2015.08.001
A catalytic synthesis of N-benzothiazol-2-yl-amides from 1-acyl-3-(phenyl)thioureas was achieved in the presence of a palladium catalyst through the C(sp2)H functionalization/CS bond formation. This synthetic methodology can produce various N-benzothiazol-2-yl-amides in high yields with good functional group tolerance.A catalytic synthesis of N-benzothiazol-2-yl-amides from 1-acyl-3-(phenyl)thioureas was achieved in the presence of a palladium catalyst through the C(sp2)H functionalization/CS bond formation.
Co-reporter:Yue Zhang, Zheng-Jun Quan, Hai-Peng Gong, Yu-Xia Da, Zhang Zhang, Xi-Cun Wang
Tetrahedron 2015 Volume 71(Issue 14) pp:2113-2118
Publication Date(Web):8 April 2015
DOI:10.1016/j.tet.2015.02.047
Co-reporter:Quanlu Yang, Zhengjun Quan, Shang Wu, Baoxin Du, Mingming Wang, Peidong Li, Yinpan Zhang, Xicun Wang
Tetrahedron 2015 Volume 71(Issue 36) pp:6124-6134
Publication Date(Web):9 September 2015
DOI:10.1016/j.tet.2015.06.103
A well-defined heterogeneous palladium catalyst, graphene oxide grafted with PdCl2, was prepared and found to be an effective catalyst for the C–C, C–N coupling of hetero aryl sulfonates with aryl boronic acids, terminal alkynes, amines, respectively, leading to the desired coupling products in moderate to excellent yields. The catalyst was characterized by XRD, IR, SEM, TEM, XPS and ICP. It is worthy noting that this catalyst offers a number of advantages such as high stability and negligible metal leaching. It also retains good activity for at least five successive runs without any additional activation treatment, showing a better performance than the well-known commercial Pd/C catalysts. This approach would be very useful from a practical viewpoint.
Co-reporter:Quanlu Yang, Shang Wu, Zhengjun Quan, Baoxin Du, Mingming Wang, Peidong Li, Yinpan Zhang, Ziqiang Lei, Xicun Wang
Tetrahedron 2015 Volume 71(Issue 44) pp:8462-8471
Publication Date(Web):4 November 2015
DOI:10.1016/j.tet.2015.09.022
This article has been retracted: please see Elsevier Policy on Article Withdrawal (http://www.elsevier.com/locate/withdrawalpolicy).This article has been retracted at the request of the authors and the editor.The figures 1-6 in the Results and Discussion section of this article were found to be very similar to a paper published in Catal. Sci. Technol., 5 (2015), 4522-4531, http://dx.doi.org/10.1039/C5CY00802F entitled ‘Wool-anchored Pd(OAc)2 complex: a highly active and reusable catalyst for desulfurative coupling reactions’’ at almost the same time by the same group. The two papers did not reference each other.
Co-reporter:Zhong-Fei Yan, Zheng-Jun Quan, Yu-Xia Da, Zhang Zhang and Xi-Cun Wang
Chemical Communications 2014 vol. 50(Issue 88) pp:13555-13558
Publication Date(Web):05 Sep 2014
DOI:10.1039/C4CC05090H
A novel method for the synthesis of the polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines through a domino desulfurative coupling–acylation–hydration and Michael addition sequence was established.
Co-reporter:Zhang Zhang, Bin Du, Zheng-Jun Quan, Yu-Xia Da and Xi-Cun Wang
Catalysis Science & Technology 2014 vol. 4(Issue 3) pp:633-638
Publication Date(Web):02 Jan 2014
DOI:10.1039/C3CY00888F
Polymer bound sulfonic acid (PEG-OSO3H) is active for the dehydration of biomass to furfural. The furfural yield is improved when MnCl2 is added to the reaction mixture. The catalyst was mild, non-volatile, and non-corrosive and can be recycled multiple times (>10) without an intermediate regeneration step and no significant leaching of –OSO3H groups is observed.
Co-reporter:Zheng-Jun Quan;Hai-Dong Xia;Zhang Zhang;Yu-Xia Da
Applied Organometallic Chemistry 2014 Volume 28( Issue 2) pp:81-85
Publication Date(Web):
DOI:10.1002/aoc.3080
N-Arylation of amides and anilines with aryl iodides was efficiently catalyzed by copper thiophenecarboxylate under ligand-free conditions with good to excellent yields. A variety of substituted aryl iodides, amides, anilines and 4-aminoantipyrine were found to be applicable to the simple catalytic system. Furthermore, some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, and 4-amino(N-phenyl)antipyrenes, which are difficult to obtain by the classical methods, were prepared. Copyright © 2013 John Wiley & Sons, Ltd.
Co-reporter:Zhang Zhang, Yu-Shan Zhang, Zheng-Jun Quan, Yu-Xia Da, Xi-Cun Wang
Tetrahedron 2014 70(47) pp: 9093-9098
Publication Date(Web):
DOI:10.1016/j.tet.2014.10.006
Co-reporter:Congde Huo;Cheng Wang;Chougu Sun;Xiaodong Jia;Xicun Wang;Wenju Chang ;Mingxia Wu
Advanced Synthesis & Catalysis 2013 Volume 355( Issue 10) pp:1911-1916
Publication Date(Web):
DOI:10.1002/adsc.201300276
Co-reporter:Zheng-Jun Quan;Wang-Hua Hu;Zhang Zhang;Yu-Xia Da;Xiao-Dong Jia
Advanced Synthesis & Catalysis 2013 Volume 355( Issue 5) pp:891-900
Publication Date(Web):
DOI:10.1002/adsc.201201097
Abstract
The molecular iodine-catalyzed three-component reaction of amides or amide derivatives, paraformaldehyde and styrenes allows for the clean generation of allylamine derivatives in good yields and high regioselectivities. The reaction, forming water as the sole co-product, is an experimentally easy to conduct transformation in the absence of transition metals under mild conditions.
Co-reporter:Zhang Zhang, Bin Du, Li-Jia Zhang, Yu-Xia Da, Zheng-Jun Quan, Liang-Jie Yang and Xi-Cun Wang
RSC Advances 2013 vol. 3(Issue 24) pp:9201-9205
Publication Date(Web):01 May 2013
DOI:10.1039/C3RA41912F
52–94% yields of 5-hydroxymethylfurfural (HMF) from carbohydrates such as monosaccharides, disaccharides and polysaccharides were achieved using PEG-OSO3H or PS-PEG-OSO3H as reusable catalysts in a DMSO/H2O reaction system. Using polymer-supported catalysis, corn stover could also be effectively transformed into HMF and furfural.
Co-reporter:Zheng-Jun Quan;Fu-Qiang Jing;Zhang Zhang;Yu-Xia Da
European Journal of Organic Chemistry 2013 Volume 2013( Issue 31) pp:7175-7183
Publication Date(Web):
DOI:10.1002/ejoc.201300592
Abstract
Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized.
Co-reporter:Zhengjun Quan;Fuqiang Jing;Zhang Zhang;Yuxia Da ;Xicun Wang
Chinese Journal of Chemistry 2013 Volume 31( Issue 12) pp:1495-1502
Publication Date(Web):
DOI:10.1002/cjoc.201300536
Abstract
Pyrimidin-2-yl sulfonates, as an efficient reaction partner, which can be easily prepared from cheap commercial materials, were coupled with phenols and anilines to give a wide array of C2-aryloxy- and arylaminopyrimidines in good to excellent yields under mild reaction conditions.
Co-reporter:Zhengjun Quan;Haidong Xia;Zhang Zhang;Yuxia Da ;Xicun Wang
Chinese Journal of Chemistry 2013 Volume 31( Issue 4) pp:501-506
Publication Date(Web):
DOI:10.1002/cjoc.201201240
Abstract
A Cu(I) generated in situ from CuSO4·5H2O/sodium ascorbate catalyzed cross-coupling reaction of aryl halides with aqueous ammonia for the synthesis of primary aromatic amines has been developed. Key to the success included the application of aqueous ammonia under a homogeneous condition.
Co-reporter:Congde Huo, Jinzhu An, Xiaolan Xu, Xiaodong Jia, Xicun Wang, Lisheng Kang
Tetrahedron Letters 2013 Volume 54(Issue 9) pp:1145-1148
Publication Date(Web):27 February 2013
DOI:10.1016/j.tetlet.2012.12.078
The reaction of chalcone epoxides with 2-naphthyl ethers can be initiated by stable triarylaminium salt. And after subsequent aerobic oxidative aromatization in one pot, a series of polysubstituted naphtho[2,1-b]furans were delivered.
Co-reporter:Zheng-Jun Quan, Ying Lv, Zhong-Jie Wang, Zhang Zhang, Yu-Xia Da, Xi-Cun Wang
Tetrahedron Letters 2013 Volume 54(Issue 14) pp:1884-1887
Publication Date(Web):3 April 2013
DOI:10.1016/j.tetlet.2013.01.113
A domino S–N and C–N coupling/oxidative aromatization process to synthesize 2-aminothio-phenylpyrimidines and 2-amino-phenylpyrimidines by S–N and C–N cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and secondary amines catalyzed by molecular iodine. Remarkably the C–N coupled product was obtained via a desulfitative coupling-aromatization reaction in one-pot reaction.
Co-reporter:Zheng-Jun Quan, Hai-Dong Xia, Zhang Zhang, Yu-Xia Da, Xi-Cun Wang
Tetrahedron 2013 69(39) pp: 8368-8374
Publication Date(Web):
DOI:10.1016/j.tet.2013.07.073
Co-reporter:Zheng-Jun Quan, Qiong Xu, Zhang Zhang, Yu-Xia Da, Xi-Cun Wang
Tetrahedron 2013 69(2) pp: 881-887
Publication Date(Web):
DOI:10.1016/j.tet.2012.10.097
Co-reporter:Xiaodong Jia, Fangfang Peng, Chang Qing, Congde Huo, and Xicun Wang
Organic Letters 2012 Volume 14(Issue 15) pp:4030-4033
Publication Date(Web):July 19, 2012
DOI:10.1021/ol301909g
A domino Csp3–H functionalization of glycine derivatives was achieved under catalytic radical cation salt induced conditions, producing a series of quinolines. The proposed mechanism shows that a peroxyl radical cation, which is generated by the coupling between O2 and TBPA+•, might be involved to initiate the catalytic oxidation.
Co-reporter:Zheng-Jun Quan;Wang-Hua Hu;Xiao-Dong Jia;Zhang Zhang;Yu-Xia Da
Advanced Synthesis & Catalysis 2012 Volume 354( Issue 16) pp:2939-2948
Publication Date(Web):
DOI:10.1002/adsc.201200402
Abstract
A domino desulfitative coupling/acylation/hydration process to synthesize C-2-(2-oxo-2-phenylethylidene)- and N-3-carbonyl-substituted pyrimidines by unprecedented CC and CN cross-coupling reactions is described. This methodology couples 3,4-dihydropyrimidine-2-thiones and alkynes under modified Liebeskind–Srogl conditions using palladium acetate and copper(I) carboxylate. Remarkably the copper(I) carboxylates simultaneously act as desulfitative and acylation reagents in the reaction.
Co-reporter:Xiao Dong Jia, Xiang Ning Chen, Cong De Huo, Fang Fang Peng, Chang Qing, Xi Cun Wang
Chinese Chemical Letters 2012 Volume 23(Issue 3) pp:309-312
Publication Date(Web):March 2012
DOI:10.1016/j.cclet.2011.12.008
Cross double Mannich reaction and tandem cyclization were achieved under iodine catalyzed conditions, yielding a series of highly substituted 4-piperidones. Among the possible diastereomers, only one diastereomer was isolated, which could be ascribed to the chair-like transition state in six-membered ring, in which all of the hindered groups are located in the pseudoequatorial orientation.
Co-reporter:Xi Cun Wang, Li Jia Zhang, Zhang Zhang, Zheng Jun Quan
Chinese Chemical Letters 2012 Volume 23(Issue 4) pp:423-426
Publication Date(Web):April 2012
DOI:10.1016/j.cclet.2012.01.016
Sulfuric acid-modified polyethylene glycol 6000 (PEG-OSO3H) was applied as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction between aldehydes, aromatic ketones and aromatic amines at room temperature using PEG400–H2O (1:1) as environment-friendly solvents. The reactions were completed in short times and mild reaction conditions with good to excellent yields.
Co-reporter:Xiaodong Jia;Xiangning Chen;Congde Huo;Fangfang Peng;Chang Qing ;Xicun Wang
Chinese Journal of Chemistry 2012 Volume 30( Issue 7) pp:1504-1510
Publication Date(Web):
DOI:10.1002/cjoc.201100717
Abstract
A multicomponent double Mannich reaction of amines, aldehydes and ketones was efficiently catalyzed by molecular iodine, producing a series of 4-piperidones in a stereoselective way. A variety of amines, aldehydes and ketones were tolerated in this tandem process, including those with labile functinal groups. Further investigation of the reaction between alkyl-imines and ketones showed that imines from amines and ketones were formed in situ and isomerized to enamine in the presence of molecular iodine to accelerate the corresponding Mannich addition.
Co-reporter:Xiaodong Jia, Chang Qing, Congde Huo, Fangfang Peng, Xicun Wang
Tetrahedron Letters 2012 Volume 53(Issue 52) pp:7140-7142
Publication Date(Web):26 December 2012
DOI:10.1016/j.tetlet.2012.10.097
A domino process between iminoethyl glyoxylate and N-vinylamides was achieved under the catalytic radical cation salt induced conditions, producing a series of quinoline-2-carboxylates. N-Vinylamides were involved as an acetylene equivalent. A possible mechanism was proposed to rationalize the formation of the products.
Co-reporter:Xicun Wang;Junling Liang;Zhengjun Quan;Lin Bai
Chinese Journal of Chemistry 2011 Volume 29( Issue 8) pp:1646-1650
Publication Date(Web):
DOI:10.1002/cjoc.201180294
Abstract
A highly ef?cient synthesis of novel pyrido[2,3-d]pyrimidin-4-ols was developed via an iodine-catalyzed tandem oxidative cyclization under focused microwave irradiation. Pyrido[2,3-d]pyrimidin-4-ols were obtained from easily available 2-amino-4-aryl-6-arylnicotinamides and benzylic amines with good to excellent yields.
Co-reporter:Zheng-Jun Quan;Rong-Guo Ren;Yu-Xia Da;Zhang Zhang
Heteroatom Chemistry 2011 Volume 22( Issue 5) pp:653-658
Publication Date(Web):
DOI:10.1002/hc.20729
Abstract
Treatment of mercapto-heterocyclic compounds with diethyl phosphite in the presence of 4-dimethylaminopyridine (DMAP) in tetrachloroethylene has given the S-ethylated product in good yields and high chemoselectivity. This procedure is compatible with a wide range of SH-compounds such as 1,3,4-oxadiazole-2-thiol, 1,3,4-thiadiazole-2-thiol, benzo[d]thiazole-2-thiol, and substituted benzenethiol. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:653–658, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20729
Co-reporter:Xi-Cun Wang, Guo-Jun Yang, Xiao-Dong Jia, Zhang Zhang, Yu-Xia Da, Zheng-Jun Quan
Tetrahedron 2011 67(18) pp: 3267-3272
Publication Date(Web):
DOI:10.1016/j.tet.2011.02.046
Co-reporter:Zheng-Jun Quan, Rong-Guo Ren, Xiao-Dong Jia, Yu-Xia Da, Zhang Zhang, Xi-Cun Wang
Tetrahedron 2011 67(13) pp: 2462-2467
Publication Date(Web):
DOI:10.1016/j.tet.2011.01.061
Co-reporter:Xiao-Dong Jia, Xiao-E Wang, Cai-Xia Yang, Cong-De Huo, Wen-Juan Wang, Yan Ren and Xi-Cun Wang
Organic Letters 2010 Volume 12(Issue 4) pp:732-735
Publication Date(Web):January 20, 2010
DOI:10.1021/ol9027978
A Mannich reaction of imines and ketones induced by persistent radical cation salts was investigated, and a series of Mannich bases, β-aminoketones, were synthesized. A novel cyclization to form the 4-piperidone skeleton was achieved in a tandem process. The reaction can be rationalized as a radical cation process supported by various evidence.
Co-reporter:Xi Cun Wang, Xiao Mei Ding, Sheng Qing Wang, Xue Fei Chen, Zheng Jun Quan
Chinese Chemical Letters 2010 Volume 21(Issue 3) pp:301-304
Publication Date(Web):March 2010
DOI:10.1016/j.cclet.2009.11.045
An environmental benign procedure for synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles has been developed by reaction of 2-amino-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with formic acid in PEG-400. The key advantages of this protocol are the shorter reaction time, higher yields, lower cost, simple workup, and environment-friendly compared to conventional organic solvent reaction. The present method does not involve any hazardous organic solvent or catalyst.
Co-reporter:Xi Cun Wang, Hai Peng Gong, Zheng Jun Quan, Lei Li, He Lin Ye
Chinese Chemical Letters 2009 Volume 20(Issue 1) pp:44-47
Publication Date(Web):January 2009
DOI:10.1016/j.cclet.2008.10.005
An efficient protocol for the one-pot multicomponent synthesis of various 2,4,5-triaryl-1H-imidazoles and 1,2,4,5-tetraaryl-1H-imidazoles using PEG-400 as reaction medium is described. This method has the advantages of good yields, less pollution and simple reaction conditions.
Co-reporter:Xi Cun Wang, Lei Li, Zheng Jun Quan, Hai Peng Gong, He Lin Ye, Xiao Feng Cao
Chinese Chemical Letters 2009 Volume 20(Issue 6) pp:651-655
Publication Date(Web):June 2009
DOI:10.1016/j.cclet.2009.02.004
Under mild conditions, conversion of a variety of ketoximes and aldoximes to their corresponding amides and nitriles proceeded in the presence of PEG-SO3H with high yields.
Co-reporter:Yu-Xia Da;Zhi Yang;Zheng-Jun Quan;Zhang Zhang
Journal of Heterocyclic Chemistry 2009 Volume 46( Issue 4) pp:737-741
Publication Date(Web):
DOI:10.1002/jhet.142
Co-reporter:Xi-Cun WANG;Zheng-Jun QUAN ;Zhang ZHANG
Chinese Journal of Chemistry 2008 Volume 26( Issue 2) pp:368-372
Publication Date(Web):
DOI:10.1002/cjoc.200890071
Abstract
An environmentally benign procedure for dimethylated 1,6-dihydropyrimidines has been developed by the reaction of 1,2,3,4-tetrahydropyrimidine-2-thiones with dimethyl carbonate, a non-toxic and environmentally friendly reagent. The methylation of 1,2,3,4-tetrahydropyrimidine-2-thione was promoted by MgO and tetrabutylammonium bromide (TBAB) under microwave. This protocol avoids the use of strong bases and highly toxic methylating agents such as methyl halide or dimethyl sulfate. Additionally, the possible role of MgO/TBAB in the reaction was also presented.
Co-reporter:Zheng-Jun Quan;Zhang Zhang;Jun-Ke Wang;Ya-Juan Liu;Peng-Yan Ji
Heteroatom Chemistry 2008 Volume 19( Issue 2) pp:149-153
Publication Date(Web):
DOI:10.1002/hc.20386
Abstract
An efficient and convenient method for thiazolo[3,2-a]pyrimidines from cyclization reaction of dihydropyrimidine-thiones with α-bromoacetone in aqueous media is described. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:149–153, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20386
Co-reporter:Xiao-Jun Liu, Wen-Peng Wang, Cong-De Huo, Xi-Cun Wang and Zheng-Jun Quan
Catalysis Science & Technology (2011-Present) 2017 - vol. 7(Issue 3) pp:NaN569-569
Publication Date(Web):2017/01/09
DOI:10.1039/C6CY02038K
An efficient and general method for Pd-catalyzed dehydrogenative aromatization of dihydro-heteroatom compounds without external O2 and H2 is first described. The protocol firstly uses isoprene as a hydrogen acceptor. Various dihydro-heterocycles including dihydropyrimidinones, dihydropyrimidines and dihydropyridines can be dehydrogenated to produce the corresponding aromatic heterocyclic compounds.
Co-reporter:Quanlu Yang, Zhengjun Quan, Baoxin Du, Shang Wu, Peidong Li, Yanxia Sun, Ziqiang Lei and Xicun Wang
Catalysis Science & Technology (2011-Present) 2015 - vol. 5(Issue 9) pp:NaN4531-4531
Publication Date(Web):2015/07/10
DOI:10.1039/C5CY00802F
A biomacromolecule-anchored palladium complex, wool-Pd(OAc)2, was prepared and characterized by IR, XPS, SEM and ICP. The new complex was used as a catalyst for the Liebeskind–Srogl desulfurative coupling reactions of pyrimidin-yl thioether derivatives with terminal alkynes and aryl boronic acids. Products were isolated in moderate to excellent yields. When 2-(phenylthio)-1,4-dihydropyrimidine derivatives were reacted with terminal alkynes and carboxyl acids, a domino reaction process was revealed. In these reactions, this novel and efficient catalyst was capable of being reused for at least nine rounds, with durable performance and wide substrate tolerance.
Co-reporter:Zhang Zhang, Bin Du, Zheng-Jun Quan, Yu-Xia Da and Xi-Cun Wang
Catalysis Science & Technology (2011-Present) 2014 - vol. 4(Issue 3) pp:NaN638-638
Publication Date(Web):2014/01/02
DOI:10.1039/C3CY00888F
Polymer bound sulfonic acid (PEG-OSO3H) is active for the dehydration of biomass to furfural. The furfural yield is improved when MnCl2 is added to the reaction mixture. The catalyst was mild, non-volatile, and non-corrosive and can be recycled multiple times (>10) without an intermediate regeneration step and no significant leaching of –OSO3H groups is observed.
Co-reporter:Zhong-Fei Yan, Zheng-Jun Quan, Yu-Xia Da, Zhang Zhang and Xi-Cun Wang
Chemical Communications 2014 - vol. 50(Issue 88) pp:NaN13558-13558
Publication Date(Web):2014/09/05
DOI:10.1039/C4CC05090H
A novel method for the synthesis of the polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines through a domino desulfurative coupling–acylation–hydration and Michael addition sequence was established.
Co-reporter:Kai-Jie Wei, Zheng-jun Quan, Zhang Zhang, Yu-xia Da and Xi-cun Wang
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 8) pp:NaN2398-2398
Publication Date(Web):2016/01/25
DOI:10.1039/C5OB02535D
The copper(I)-promoted cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with aromatic amines and aliphatic amines to deliver C–N coupling products in moderate to good yields is reported in this paper. Central to this strategy is the conversion of disulfides into aryl- and alkyl amines by a copper-promoted chemoselective C–S bond cleavage.