Co-reporter:Ruihua Wu;Wen Yang;Wenkun Chen;Dingqiao Yang
Organic Chemistry Frontiers 2017 vol. 4(Issue 10) pp:1921-1925
Publication Date(Web):2017/09/26
DOI:10.1039/C7QO00420F
A new efficient platinum-catalyzed ring-opening reaction of oxabicyclic alkenes with a wide range of sodium arylsulfinates was developed, affording the desired products 3 or 4 in good to excellent yields under mild conditions. This protocol provides a new low-cost, viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ols 3 and 2-aryl-naphthalenes 4 with good functional group tolerance. To the best of our knowledge, it represents the first example in the ring-opening reactions of oxabicyclic alkenes with sodium arylsulfinates via a platinum catalyst and desulfonylation using the Pt catalyst. In addition, a plausible mechanism for the ring-opening reaction was also proposed.
Co-reporter:Wei Guo, Lv-Yin Zheng, Yong-Dong Li, Ren-Miao Wu, Qiang Chen, Ding-Qiao Yang, Xiao-Lin Fan
European Journal of Medicinal Chemistry 2016 Volume 115() pp:291-294
Publication Date(Web):10 June 2016
DOI:10.1016/j.ejmech.2016.03.037
•3-Substituted quinazolinones were discovered by a scaffold hopping approach from salicylanilides.•The compound 3p displayed excellent molluscicidal and cercaricidal activities, as well as low toxicity.•The novel design strategy offers an effective and environment-friendly approach for the control of Schistosomiasis.Discovery of novel topological agents against Oncomelania hupensis snails and cercariae remains a significant challenge in current Schistosomiasis control. A pseudo-ring formed from salicylanilide by an intramolecular hydrogen bond led to the discovery of 3-substituted quinazolinone derivatives which showed a potent molluscicidal and cercaricidal activities.A pseudo-ring formed from salicylanilide by an intramolecular hydrogen bond led to the discovery of 3-substituted quinazolinone derivatives which showed a potent molluscicidal and cercaricidal activities.
Co-reporter:Meixiang Lv;Chunfeng Yao;Dingqiao Yang;Heping Zeng
Journal of Applied Polymer Science 2016 Volume 133( Issue 25) pp:
Publication Date(Web):
DOI:10.1002/app.43555
ABSTRACT
The halogen-free flame retardance of natural fiber is an everlasting challenge due to the well-known poor solubility of phosphazene in water. In this case, a new cyclotriphosphazene derivative (MCP) was synthesized. It was etherized hexamethylolmelamine (HMMM) and hexachloro-cyclotriphosphazene (HCCP) by one pot reaction. It was characterized by 1H NMR, 13C NMR, 31P NMR, FT-IR, TGA, SEM, limited oxygen index (LOI) and vertical flame testing. The MCP has good solubility in water and thermosetting MCP has compact structure which can expand several times after burning. Cotton gauze was soaked in six different concentration of aqueous solutions of MCP (0 wt %, 5 wt %, 10 wt %, 15 wt %, 20 wt % and 25 wt %, respectively) to obtain the flame retardant cloth. The cloth was soaked in 20 wt % MCP solution had higher char yield and LOI. They had no any afterflame and afterglow, and gauze 2- gauze 5 cannot be burned out in 12s ignition time. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43555.
Co-reporter:Guo Cheng, Wen Yang, Yue Li, and Dingqiao Yang
The Journal of Organic Chemistry 2016 Volume 81(Issue 17) pp:7817-7823
Publication Date(Web):July 25, 2016
DOI:10.1021/acs.joc.6b01479
Cooperative catalysis has been widely considered as one of the most powerful strategies to improve synthetic efficiency. A new iridium/copper cocatalyst was developed for the ring-opening reaction of oxabenzonorbornadienes with a wide variety of Grignard reagents, which afforded the corresponding anti-2-substituted 1,2-dihydronaphthalen-1-ols in high yields (up to 99% yield) under mild conditions. The effects of catalyst loading, Lewis acid, Grignard reagent loading, and reaction temperature on the yield were investigated. To the best of our knowledge, it represents the first example of ring-opening reactions of oxabicyclic alkenes with Grignard reagent nucleophiles in a trans-stereoselective manner.
Co-reporter:Yue Li, Wen Yang, Guo Cheng, and Dingqiao Yang
The Journal of Organic Chemistry 2016 Volume 81(Issue 11) pp:4744-4750
Publication Date(Web):May 6, 2016
DOI:10.1021/acs.joc.6b00667
Palladium-catalyzed syn-stereocontrolled ring-opening reactions of oxabenzonorbornadienes with a wide range of sodium arylsulfinates were investigated, affording the desired products in good to excellent yields under an air atmosphere. This protocol provides a low-cost new viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ol with good functional group tolerance. In addition, the cis configuration of 3da was established by X-ray diffraction analysis, and a plausible mechanism for the ring-opening reaction was proposed.
Co-reporter:Guobao Huang, Zhenfeng He, Chen-Xi Cai, Fangfang Pan, Dingqiao Yang, Kari Rissanen and Wei Jiang
Chemical Communications 2015 vol. 51(Issue 85) pp:15490-15493
Publication Date(Web):26 Aug 2015
DOI:10.1039/C5CC06768E
Two configurational isomers of bis-urea macrocycles have been synthesized, and their neutral molecule recognition was studied by X-ray crystallography and 1H NMR experiments. Cooperative action between the deep cavity and the urea groups and the influence of dipole alignments on molecular recognition are discussed.
Co-reporter:Ling Meng, Wen Yang, Xuejing Pan, Meng Tao, Guo Cheng, Sanyong Wang, Heping Zeng, Yuhua Long, and Dingqiao Yang
The Journal of Organic Chemistry 2015 Volume 80(Issue 5) pp:2503-2512
Publication Date(Web):February 13, 2015
DOI:10.1021/acs.joc.5b00065
A platinum(II)-catalyzed asymmetric ring opening of oxabenzonorbornadienes with phenols was developed, which afforded the corresponding cis-2-(un)substituted phenoxy-1,2-dihydronaphthalen-1-ol products rather than the trans ones in excellent yields (up to 99%) with moderate to good enantioselectivities (up to 87% ee) under mild conditions. In addition, the cis-configuration of product 2b was confirmed by X-ray diffraction analysis. Based on the results, a potential mechanism for the present catalytic reaction was proposed.
Co-reporter:Dingqiao Yang and Ni Liang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 13) pp:2080-2086
Publication Date(Web):24 Jan 2014
DOI:10.1039/C3OB42199F
A new platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with various Grignard reagents was reported, which afforded the corresponding anti-2-substituted-1,2-dihydronaphthalen-1-ol products with moderate to good yields in the presence of a catalytic amount of Pt(PPh3)4 (2.5 mol%) under mild conditions. The effects of catalyst loading, solvent and temperature on the yield were also investigated. Furthermore, the trans-configuration of the product 5i was confirmed by X-ray diffraction analysis.
Co-reporter:Yuhua Long;Xiaolu Li;Xuejing Pan;Dandan Ding;Xuan Xu;Xiongjun Zuo
Catalysis Letters 2014 Volume 144( Issue 3) pp:419-433
Publication Date(Web):2014 March
DOI:10.1007/s10562-013-1136-x
A novel iridium-catalyzed asymmetric ring-opening of oxabicyclic alkenes with a variety of carboxylic acids was reported, which afforded the corresponding trans-carboxylic acids 1-hydroxy-1,2-dihydro-naphthalen-2-yl ester products in good yields with moderate enantioselectivities under mild conditions. The trans products are formed via the enantioselective cleavage of a bridgehead carbon–oxygen bond in 1 followed by SN2′ nucleophilic attack by carboxylic acids. The effects of various bisphosphine ligands, Ag(I) salts, ammonium halides, bases, and solvents on the yields and enantioselectivities of the reaction were also investigated. The theoretical analysis of stability and hydrogen bond for 1-hydroxy-1,2-dihydronaphthalen-2-yl 4-chlorobenzoate 2a were performed using the density functional theory B3LYP methods. The trans-configuration of the product 2a was confirmed by X-ray diffraction analysis. A possible mechanism for the present catalytic reaction was proposed.
Co-reporter:Xuejing Pan, Guobao Huang, Yuhua Long, Xiongjun Zuo, Xuan Xu, Fenglong Gu, and Dingqiao Yang
The Journal of Organic Chemistry 2014 Volume 79(Issue 1) pp:187-196
Publication Date(Web):November 25, 2013
DOI:10.1021/jo402386k
A new platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes was developed, which afforded the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol products in high yields (up to 97%) with moderate to good enantioselectivities (up to 89% ee) under very mild conditions. The effects of various ligands, catalyst loading, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. The cis configuration of product 2m was confirmed by X-ray diffraction analysis. A potential mechanism for the present catalytic reaction is proposed.
Co-reporter:Zhongyi Zeng, Dingqiao Yang, Yuhua Long, Xuejing Pan, Guobao Huang, Xiongjun Zuo, and Wen Zhou
The Journal of Organic Chemistry 2014 Volume 79(Issue 11) pp:5249-5257
Publication Date(Web):May 13, 2014
DOI:10.1021/jo500821m
A new, versatile, and highly efficient nickel-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of arylboronic acids has been developed, yielding cis-2-aryl-1,2-dihydronaphthalen-1-ols in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under very mild conditions. The effects of various nickel precursors, chiral bidentate ligands, catalyst loadings, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding cis-ring-opened products based on the X-ray structure of product 4b.
Co-reporter:Dingqiao Yang, Jiuyun Xia, Yuhua Long, Zhongyi Zeng, Xiongjun Zuo, Sanyong Wang and Chunrong Li
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 29) pp:4871-4881
Publication Date(Web):23 May 2013
DOI:10.1039/C3OB40891D
A novel asymmetric ring-opening reaction of N-substituted azabenzonorbornadienes with a wide variety of substituted benzyl alcohols and the addition reaction of N-substituted azabenzonorbornadienes with thiols are reported, affording the corresponding 1,2-trans-alkoxyamino products in moderate yields with excellent enantioselectivities (up to 94% ee) and the corresponding thiol addition products in high yields with lower enantiomeric excesses (ee) in the presence of iridium catalyst, respectively. The effects of ligands, catalyst loading, solvents and additives, and temperature were also investigated. The anti-configuration of the product 3c was confirmed by X-ray crystal structure analysis. A possible mechanism for the present catalytic reaction is proposed.
Co-reporter:Wenling Wang;Yuhua Long;Zhifu Zou ;Dingqiao Yang
Chinese Journal of Chemistry 2012 Volume 30( Issue 5) pp:1092-1096
Publication Date(Web):
DOI:10.1002/cjoc.201100679
Abstract
This work reported a convenient method for the preparation of enantiomerically pure 6-aryl-2,2′-dihydroxy-1,1′-binaphthyl derivatives starting from the commercially available (R)-2,2′-hydroxy-1,1′-binaphthyl [(R)-1] via bromination, hydrolysis and Suzuki cross coupling reaction. This novel synthetic method was characterized with high regioselectivity, simple operation, mild reaction conditions, and excellent yield (up to 73%). On the other hand, we synthesized the target unknown compounds, which were confirmed by IR, 1H NMR, 13C NMR, MS and elementary analysis.
Co-reporter:Shai Fang, Xiuli Liang, Yuhua Long, Xiaolu Li, Dingqiao Yang, Sanyong Wang, and Chunrong Li
Organometallics 2012 Volume 31(Issue 8) pp:3113-3118
Publication Date(Web):March 26, 2012
DOI:10.1021/om3000295
The asymmetric ring-opening of azabicyclic alkenes with a variety of phenols is investigated using an iridium catalyst generated in situ from 2.5 mol % of [Ir(COD)Cl]2 and 5.0 mol % of (S)-BINAP, which afforded the corresponding 1,2-trans-phenoxyamino products in excellent yield (up to 92%) with moderate to good enantioselectivities (up to 98% ee). The trans-configuration of the product 4b was confirmed by X-ray crystallography.
Co-reporter:Hanchao Cheng and Dingqiao Yang
The Journal of Organic Chemistry 2012 Volume 77(Issue 21) pp:9756-9765
Publication Date(Web):October 8, 2012
DOI:10.1021/jo3018507
A novel iridium-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a variety of phenols was reported, which afforded the corresponding trans-2-phenoxy-1,2-dihydronaphthalen-1-ol products in high yields with moderate to excellent enantioselectivities (up to 98% ee) under mild conditions. The trans products are formed via the enantioselective cleavage of a bridgehead carbon–oxygen bond in 1 followed by SN2 nucleophilic attack by phenols. The effects of various bisphosphine ligands, Ag (I) salts, ammonium halides, bases, and solvents on the yield and enantioselectivity of the reaction were also investigated. The trans-configuration of the product 2a was confirmed by X-ray crystal structure analysis. A possible mechanism for the present catalytic reaction was proposed.
Co-reporter:Yuhua Wu;Dingqiao Yang;Heping Zeng;Lei Xie;Lihuan Wu;Haihong Mo ;Xiongjun Zuo
Chinese Journal of Chemistry 2010 Volume 28( Issue 2) pp:235-242
Publication Date(Web):
DOI:10.1002/cjoc.201090059
Abstract
Asymmetric ring-opening reactions of N-Boc-azabenzonorbornadiene with N-substituted piperazine nucleophiles in the presence of 5 mol% of [Rh(COD)Cl]2 and 10 mol% of chiral ligand, (R,S)-PPF-P-t-Bu2, gave the corresponding 1,2-diamine product in moderate to excellent yields (up to 95%) with reasonable enantiomeric excesses (up to 70% ee). The results showed that the nature of ligands had significant influence on the yields and the enantiomeric excesses.
Co-reporter:Yuhua Long;Shuangqi Zhao;Heping Zeng;Dingqiao Yang
Catalysis Letters 2010 Volume 138( Issue 1-2) pp:124-133
Publication Date(Web):2010 August
DOI:10.1007/s10562-010-0383-3
Rhodium-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadienes with aliphatic primary amines and substituted N-phenylpiperazines were investigated. These reactions are featured with the formation of a new carbon-nitrogen bond via an intermolecular allylic displacement of the bridgehead oxygen with amine nucleophiles, which offered the corresponding products in good to excellent yields (up to 97%) with excellent enantioselectivities (up to 99%ee).
Co-reporter:Dingqiao Yang, Yuhua Long, Yujuan Wu, Xiongjun Zuo, Qingqiang Tu, Shai Fang, Lasheng Jiang, Sanyong Wang, and Chunrong Li
Organometallics 2010 Volume 29(Issue 22) pp:5936-5940
Publication Date(Web):October 25, 2010
DOI:10.1021/om100722f
A novel iridium-catalyzed ring-opening reaction of azabicyclic alkenes with a variety of primary aromatic amines is reported, which afforded the corresponding 1,2-trans-diamine derivatives in high yields (up to 96%) with excellent enantioselectivities (up to 97% ee) under relatively mild conditions. The trans configuration of product 2b was confirmed by X-ray crystallography.
Co-reporter:Dingqiao Yang, Yuhua Long, Junfang Zhang, Heping Zeng, Sanyong Wang and Chunrong Li
Organometallics 2010 Volume 29(Issue 16) pp:3477-3480
Publication Date(Web):July 15, 2010
DOI:10.1021/om100384q
We have explored a new iridium-catalyzed ring-opening reaction of oxabenzonorbornadienes with a variety of primary aromatic amine or N-substituted piperazine nucleophiles, affording the corresponding products in excellent yields (up to 99%) with moderate enantioselectivity (25−81% ee). The trans configuration of product 2d was confirmed by X-ray crystallography.
Co-reporter:Yuhua Long, Dingqiao Yang, Zhenming Zhang, Yujuan Wu, Heping Zeng, and Yu Chen
The Journal of Organic Chemistry 2010 Volume 75(Issue 21) pp:7291-7299
Publication Date(Web):October 13, 2010
DOI:10.1021/jo101470r
The enantioselective ring-opening reactions of azabicyclic alkenes with primary and secondary aromatic amine nucleophiles are reported using an iridium catalyst generated in situ from 1.5 mol % of [Ir(COD)Cl]2 and 3 mol % of (S)-BINAP. The reaction affords the corresponding trans-1,2-diamine derivatives in moderate to good yields with moderate to high enantioselectivities (up to 97% ee). The trans-configuration of the 1,2-diamino product 2g was confirmed by X-ray crystallography.
Co-reporter:Dingqiao Yang;Wei Guo;Yuepeng Cai;Lasheng Jiang;Kailing Jiang ;Xiaobing Wu
Heteroatom Chemistry 2008 Volume 19( Issue 3) pp:229-233
Publication Date(Web):
DOI:10.1002/hc.20356
Abstract
Novel quinolines fused with a six-member ring 5a–j were prepared in high yields (75–95%) via the Friedländer reaction of dimethoxy-substituted o-aminobenzaldehydes of 3a or 3b with cyclic ketones 4, respectively. The structures of 5a–j were determined by IR, 1H NMR, MS, and elemental analysis. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:229–233, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20356
Co-reporter:Guobao Huang, Zhenfeng He, Chen-Xi Cai, Fangfang Pan, Dingqiao Yang, Kari Rissanen and Wei Jiang
Chemical Communications 2015 - vol. 51(Issue 85) pp:NaN15493-15493
Publication Date(Web):2015/08/26
DOI:10.1039/C5CC06768E
Two configurational isomers of bis-urea macrocycles have been synthesized, and their neutral molecule recognition was studied by X-ray crystallography and 1H NMR experiments. Cooperative action between the deep cavity and the urea groups and the influence of dipole alignments on molecular recognition are discussed.
Co-reporter:Dingqiao Yang, Jiuyun Xia, Yuhua Long, Zhongyi Zeng, Xiongjun Zuo, Sanyong Wang and Chunrong Li
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 29) pp:NaN4881-4881
Publication Date(Web):2013/05/23
DOI:10.1039/C3OB40891D
A novel asymmetric ring-opening reaction of N-substituted azabenzonorbornadienes with a wide variety of substituted benzyl alcohols and the addition reaction of N-substituted azabenzonorbornadienes with thiols are reported, affording the corresponding 1,2-trans-alkoxyamino products in moderate yields with excellent enantioselectivities (up to 94% ee) and the corresponding thiol addition products in high yields with lower enantiomeric excesses (ee) in the presence of iridium catalyst, respectively. The effects of ligands, catalyst loading, solvents and additives, and temperature were also investigated. The anti-configuration of the product 3c was confirmed by X-ray crystal structure analysis. A possible mechanism for the present catalytic reaction is proposed.
Co-reporter:Dingqiao Yang and Ni Liang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 13) pp:NaN2086-2086
Publication Date(Web):2014/01/24
DOI:10.1039/C3OB42199F
A new platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with various Grignard reagents was reported, which afforded the corresponding anti-2-substituted-1,2-dihydronaphthalen-1-ol products with moderate to good yields in the presence of a catalytic amount of Pt(PPh3)4 (2.5 mol%) under mild conditions. The effects of catalyst loading, solvent and temperature on the yield were also investigated. Furthermore, the trans-configuration of the product 5i was confirmed by X-ray diffraction analysis.