- One-pot synthesis of 3-substituted-4H-[1,2,3] triazolo[5,1-c][1,4]oxazin-6(7H)-ones from propargyl alcohols, chloroacetyl chloride, and sodium azide
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An efficient, one-pot synthesis of 3-substituted-4H-[1,2,3]triazolo[5,1-c][1,4]oxazin-6(7H)-ones is developed via sequential esterification, substitution, and 1,3-dipolar cycloaddition processes of various propargyl alcohols, chloroacetyl chloride, and so
- Chen, Jun-Min,Liu, Xiao-Ling,Sheng, Shou-Ri,Wei, Mei-Hong,Zhang, Xiao-Lan
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- Bi(OTf)3-catalyed One-pot Synthesis of α-Halo-β-amino Ketones and Acyl Aziridines from 3-Aryl Propargyl Alcohols
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A Bi(OTf)3-catalyed reaction of 3-aryl propargyl alcohols with sulfonamide and halogen source was firstly investigated, which provided a facile route for the synthesis of a large variety of α-halo-β-amino ketones. The key intermediates, β-amino
- Zhang, Qinglin,Duan, Yongbin,Guo, Huifeng,Yang, Hong,Zhai, Jiulong,Li, Tiantian,Wang, Zhihai,Lu, Xiaolei,Wang, Yan,Yin, Yan
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supporting information
p. 1832 - 1838
(2021/06/09)
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- Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
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Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
- Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
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supporting information
p. 1553 - 1558
(2021/02/26)
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- Unified Approach to Furan Natural Products via Phosphine-Palladium Catalysis
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Polyalkyl furans are widespread in nature, often performing important biological roles. Despite a plethora of methods for the synthesis of tetrasubstituted furans, the construction of tetraalkyl furans remains non-trivial. The prevalence of alkyl groups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkyl furans, calls for a general synthetic protocol for polyalkyl furans. This paper describes a Michael–Heck approach, using sequential phosphine-palladium catalysis, for the preparation of various polyalkyl furans from readily available precursors. The versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes, namely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran; the marine natural products plakorsins A, B, and D and plakorsin D methyl ester; and the furan fatty acids 3D5 and hydromumiamicin.
- Chen, Violet Yijang,Kwon, Ohyun
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supporting information
p. 8874 - 8881
(2021/03/17)
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- Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde
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A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.
- Chen, Xiaojuan,Fu, Liping,Huo, Xiaoli,Shao, Jiaan,Yu, Liya,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian
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supporting information
p. 16430 - 16433
(2021/10/01)
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- Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst
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The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions.
- Brzozowska, Aleksandra,Zubar, Viktoriia,Ganardi, Ruth-Christine,Rueping, Magnus
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supporting information
p. 3765 - 3769
(2020/04/15)
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- Catalytic claisen rearrangement by intercepting ketenimines with propargylic alcohols: A strategy to generate and transform ketenimines from radicals
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An efficient strategy for facilitating the cross-coupling of two radicals has been established via the coordination of a radical with a metal catalyst. This strategy provides a remarkable ability to harness the reactivity of nitrile-containing azoalkanes and enables a novel cascade reaction with nitrile-containing azoalkanes and propargylic alcohols to be established. By using this reaction, a range of acetylenic and allenic amides were obtained that provides a versatile platform for further derivatizations.
- Yan, Xuyang,Liu, Hongchi,Wei, Shenquan,Huang, Hanmin
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supporting information
p. 6794 - 6798
(2020/09/15)
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- Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines
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A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.
- Chen, Zhengwang,Liang, Pei,Ma, Xiaoyue,Luo, Haiqing,Xu, Guohai,Liu, Tanggao,Wen, Xiaowei,Zheng, Jing,Ye, Hui
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supporting information
p. 1630 - 1639
(2019/01/26)
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- Metal-free aminothiation of alkynes: Three-component tandem annulation toward indolizine thiones from 2-alkylpyridines, ynals, and elemental sulfur
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A metal-free three-component annulation reaction for the synthesis of indolizine thiones via tandem C-C/C-N/C-S bond formation was developed. Various 2-alkylpyridines with aromatic ynals and elemental sulfur proceeded smoothly under catalyst-free conditions, and the desired products were obtained in moderate to excellent yields.
- Chen, Zhengwang,Liang, Pei,Xu, Fan,Deng, Zhen,Long, Lipeng,Luo, Guotian,Ye, Min
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supporting information
p. 12639 - 12647
(2019/10/11)
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- Metal-Free Regioselective Chloroazidation of Internal Alkynes
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A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.
- Huang, Bin,Liffert, Raphael,Linden, Anthony,Gademann, Karl
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supporting information
p. 981 - 984
(2019/01/04)
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- Palladium-Catalyzed Nitrile-Assisted C(sp3)-Cl Bond Formation for Synthesis of Dichlorides
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A palladium-catalyzed coupling procedure of alkenes with alkynylnitriles has been demonstrated for the synthesis of dichlorides. The reaction is the first example of nitrile-assisted C(sp3)-Cl formation promoted by coordination of a cyano group with an alkylpalladium(II) complex. The construction of a five-membered cycle intermediate successfully inhibits the β-hydride abstraction, resulting in direct C-Cl bond reductive elimination of alkylpalladium(II) chloride.
- He, Dandan,Huang, Liangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 8308 - 8311
(2019/10/16)
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- Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis
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We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.
- Shi, Taoda,Teng, Shenghan,Gopi Krishna Reddy, Alavala,Guo, Xin,Zhang, Yueteng,Moore, Kohlson T.,Buckley, Thomas,Mason, Damian J.,Wang, Wei,Chapman, Eli,Hu, Wenhao
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supporting information
p. 8737 - 8744
(2019/10/16)
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- Regioselective Synthesis of Indene from 3-Aryl Propargylic gem-Dipivalates Catalyzed by N-Heterocyclic Carbene Gold(I) Complexes
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1-Aryl-3,3-bis(pivaloyloxy)propynes can be converted in good to high yields into either 1,3- or 1,2-bis(pivaloyloxy)indenes, depending on the N-heterocyclic carbene (NHC) gold(I) hexafluoroantimonate catalyst used. Almost exclusive formation of 1,3-di(oxycarbonyl)indene derivatives was achieved with cationic gold complexes containing the embracing N,N′-1,3-bis(9-butylfluorenyl)benzimidazolylidene ligand (nBuFNHC). The regioselective issue of the reaction was rationalized by the specific spatial distribution of the steric bulk in the nBuFNHC ligand. In contrast, only modest selectivities in favor of 1,2-disubstituted indenes were observed with more classical NHC gold complexes, the best selectivity being then obtained with N,N′-1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolylidene gold chloride (SIPrAuCl) as precatalyst. (Figure presented.).
- Hueber, Damien,Teci, Matthieu,Brenner, Eric,Matt, Dominique,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien
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supporting information
p. 2453 - 2459
(2018/05/14)
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- Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect
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A highly enantioselective [2,3] Wittig rearrangement of oxindole derivatives was realized by using a chiral N,N′-dioxide/NiII complex as the catalyst under mild reaction conditions. A strong chiral amplification effect was observed, and allowed access to chiral 3-hydroxy 3-substituted oxindoles bearing allenyl groups in high yields and enantioselectivities (up to 92 % ee) by using a ligand with only 15 % ee. A reasonable explanation was given based on the experimental investigations and X-ray crystal structures of enantiomerically pure and racemic catalysts. Moreover, the first catalytic kinetic resolution of racemic oxindole derivatives by a [2,3] Wittig rearrangement was realized with high efficiency and stereoselectivity.
- Xu, Xi,Zhang, Jianlin,Dong, Shunxi,Lin, Lili,Lin, Xiaobin,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 8734 - 8738
(2018/07/14)
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- Design and synthesis of novel xanthine derivatives as potent and selective A2B adenosine receptor antagonists for the treatment of chronic inflammatory airway diseases
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Adenosine induces bronchial hyperresponsiveness and inflammation in asthmatics through activation of A2B adenosine receptor (A2BAdoR). Selective antagonists have been shown to attenuate airway reactivity and improve inflammatory cond
- Basu, Sujay,Barawkar, Dinesh A.,Ramdas, Vidya,Patel, Meena,Waman, Yogesh,Panmand, Anil,Kumar, Santosh,Thorat, Sachin,Naykodi, Minakshi,Goswami, Arnab,Reddy, B. Srinivasa,Prasad, Vandna,Chaturvedi, Sandhya,Quraishi, Azfar,Menon, Suraj,Paliwal, Shalini,Kulkarni, Abhay,Karande, Vikas,Ghosh, Indraneel,Mustafa, Syed,De, Siddhartha,Jain, Vaibhav,Banerjee, Ena Ray,Rouduri, Sreekanth R.,Palle, Venkata P.,Chugh, Anita,Mookhtiar, Kasim A.
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p. 218 - 229
(2017/04/19)
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- Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides
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The first highly enantioselective, diastereoselective, and regioselective [2,3]-rearrangement of iodonium ylides has been developed as a general solution to catalytic onium ylide rearrangements. In the presence of a chiral copper catalyst, substituted allylic iodides couple with α-diazoesters to generate metal-coordinated iodonium ylides, which undergo [2,3]-rearrangements with high selectivities (up to >95:5 r.r., up to >95:5 d.r., and up to 97 % ee). The enantioenriched iodoester products can be converted stereospecifically into a variety of onium ylide rearrangement products, as well as compounds that are not accessible by classical onium ylide rearrangements.
- Xu, Bin,Tambar, Uttam K.
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supporting information
p. 9868 - 9871
(2017/08/08)
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- Gold(I)-Initiated Cycloisomerization/Diels-Alder/Retro-Diels-Alder Cascade Strategy to Biaryls
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A unique approach to biaryls was developed on the basis of propargyl vinyl ethers and dienophiles substrates via a gold(I)-initiated cycloisomerization/Diels-Alder/retro-Diels-Alder cascade reaction. The scope and mechanism of the reaction were investigated on the basis of a series of synthetic substrates, control experiments, and DFT calculations.
- Jin, Shengfei,Niu, Yujie,Liu, Chengjun,Zhu, Lifeng,Li, Yangming,Cui, Shanshan,Xiong, Zhiling,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
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p. 9066 - 9074
(2017/09/11)
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- Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels–Alder Reactions
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An asymmetric carbene cascade reaction, which proceeds through carbene/alkyne metathesis and formal (3+2) cycloaddition and converts alkynyl-tethered enol diazoacetates to chiral bicyclic cyclopentadienes, is presented; and no catalytic asymmetric version of these carbene cascade transformations has been disclosed so far. The proton signals of the cyclopropene intermediates are observed in the mechanism study, which clearly demonstrate the reaction pathways. In addition, these products are intercepted via Diels–Alder reactions to provide bridged polycyclic structures in high yields and enantioselectivities. (Figure presented.).
- Wang, Xiangbo,Zhou, Yunfei,Qiu, Lihua,Yao, Ruwei,Zheng, Yang,Zhang, Cheng,Bao, Xiaoguang,Xu, Xinfang
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supporting information
p. 1571 - 1576
(2016/10/13)
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- Palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides
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A palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides is reported. Remarkably, the orderly insertion of isocyanides affords two types of valuable N-heterocyclic products (Z)-6-imino-4,6-dihydro-1H-furo[3,4-b]pyrrol-2-amines and (E)-5-iminopyrrolones in high yields. Systematic analysis of the reaction conditions indicates that the selectivity of these N-heterocyclic products can be controlled by ligands and temperature.
- Peng, Jianwen,Gao, Yang,Hu, Weigao,Gao, Yinglan,Hu, Miao,Wu, Wanqing,Ren, Yanwei,Jiang, Huanfeng
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supporting information
p. 5924 - 5927
(2016/11/29)
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- Gold(I)-Catalyzed Angle Strain Controlled Strategy to Furopyran Derivatives from Propargyl Vinyl Ethers: Insight into the Regioselectivity of Cycloisomerization
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A unique strategy for the regiospecific synthesis of bicyclic furopyran derivatives has been developed via a gold(I)-catalyzed propargyl-Claisen rearrangement/6-endo-trig cyclization of propargyl vinyl ethers. The introduction of angle strain into the substrates significantly altered the reaction's regioselectivity. Insight into the regioselectivity of the cycloisomerization was obtained with density functional theory calculations. (Chemical Equation).
- Jin, Shengfei,Jiang, Chongguo,Peng, Xiaoshi,Shan, Chunhui,Cui, Shanshan,Niu, Yuanyuan,Liu, Yang,Lan, Yu,Liu, Yongxiang,Cheng, Maosheng
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supporting information
p. 680 - 683
(2016/03/01)
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- A gold(i)-catalyzed substituent-controlled cycloisomerization of propargyl vinyl ethers to multi-substituted furofuran and furopyran derivatives
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A gold(i)-catalyzed substituent-controlled strategy for the stereoselective synthesis of bicyclic furan and pyran derivatives has been developed. The mechanisms of the reactions have been studied thoroughly by deuterium labelling experiments. The applications of the methodologies were demonstrated by evaluating the preliminary anti-fungal activity of the synthetic compounds.
- Liu, Yongxiang,Jin, Shengfei,Wang, Yanshi,Cui, Shanshan,Peng, Xiaoshi,Niu, Yuanyuan,Du, Chuan,Cheng, Maosheng
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supporting information
p. 6233 - 6236
(2016/05/24)
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- Pd(ii)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols to form 2,5-dihydrofurans
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A Pd(ii)-catalyzed formal [4+1] cycloaddition of aryl diazoacetates and aryl propargyl alcohols is reported to afford 2,5-dihydrofuran derivatives as the dominant product over other traditional ones. The auto-tandem catalytic process is proposed to occur via Pd(ii)-catalyzed intermolecular oxonium ylide formation and subsequent intramolecular trapping of the ylide with Pd(ii)-activated alkynes.
- Shi, Taoda,Guo, Xin,Teng, Shenghan,Hu, Wenhao
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supporting information
p. 15204 - 15207
(2015/10/12)
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- Palladium-catalyzed nucleophilic substitution of propargylic carbonates and meldrum's acid derivatives
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The palladium-catalyzed reaction of propargylic carbonates with Meldrum's acid derivatives proceeds smoothly in the presence of Pd(OAc)2 and P(2-furyl)3 in THF at 80 °C to give substitution products. The substitution products can be
- Ambrogio, Ilaria,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Iazzetti, Antonia
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p. 3147 - 3151
(2015/05/13)
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- Click chemistry route to tricyclic monosaccharide triazole hybrids: Design and synthesis of substituted hexahydro-4H-pyrano[2,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepines
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A click chemistry approach to novel tricyclic monosaccharide triazole hybrids, namely, aryl substituted hexahydro-4H-pyrano[2,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine derivatives from an intramolecular 1,3-dipolar cycloaddition of 6-azido-4-O-propargyl glycopyranosides has been reported.
- Konda, Saidulu,Rao, Pallavi,Oruganti, Srinivas
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p. 63962 - 63965
(2015/02/19)
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- Zinc-catalyzed [4+3] cycloaddition with concomitant furan annulation: Formation of cyclohepta[b]furans
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A convenient zinc-promoted [4+3] cycloaddition of a carbonyl ene-yne with simple dienes was first achieved. This reaction provided an efficient strategy to prepare various cyclohepta[b]furan rings by cascade cycloadditions. Additionally, a multicomponent reaction of dione, alkynal, and diene was also reported, which exhibited a novel strategy for selective creations of C-O bonds and C-C bonds. Go tandem! A first zinc-catalyzed tandem [4+3] cycloaddition is presented herein. Various substituted cyclohepta[b]furans were synthesized from carbonyl ene-yne and diene in moderate to good yield. Furan rings and seven-membered rings were prepared in one single step (see scheme; TBS=tert-butyldimethyl).
- Song, Bo,Li, Lian-Hua,Song, Xian-Rong,Qiu, Yi-Feng,Zhong, Mei-Jin,Zhou, Ping-Xin,Liang, Yong-Min
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supporting information
p. 5910 - 5913
(2014/05/20)
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- Bronsted acid catalyzed and NIS-promoted cyclization of diynones: Selective synthesis of 4-pyrone, 4-pyridone, and 3-pyrrolone derivatives
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Bronsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Bronsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.
- Qiu, Yi-Feng,Yang, Fang,Qiu, Zi-Hang,Zhong, Mei-Jin,Wang, Li-Jing,Ye, Yu-Ying,Song, Bo,Liang, Yong-Min
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p. 12018 - 12028
(2014/01/06)
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- Lactone radical cyclizations and cyclization cascades mediated by SmI 2-H2O
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Unsaturated lactones undergo reductive radical cyclizations upon treatment with SmI2-H2O to give decorated cycloheptanes in a single highly selective operation during which up to three contiguous stereocenters are generated. Furthermore, cascade processes involving lactones bearing two alkenes, an alkene and an alkyne, or an allene and an alkene allow "one-pot" access to biologically significant molecular scaffolds with the construction of up to four contiguous stereocenters. The cyclizations proceed by the trapping of radical anions formed by electron transfer reduction of the lactone carbonyl.
- Parmar, Dixit,Matsubara, Hiroshi,Price, Kieran,Spain, Malcolm,Procter, David J.
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supporting information; experimental part
p. 12751 - 12757
(2012/09/05)
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- Palladium-catalyzed synthesis of 2-amino ketones from propargylic carbonates and secondary amines
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A novel palladium-catalyzed approach to 2-amino ketones from arylpropargylic carbonates bearing neutral, electron-rich, and electron-poor aromatic rings and cyclic secondary amines containing useful functional groups such as cyano, chloro, and bromo subst
- Cacchi, Sandro,Fabrizi, Giancarlo,Filisti, Eleonora,Goggiamani, Antonella,Iazzetti, Antonia,Maurone, Loredana
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supporting information; experimental part
p. 4699 - 4703
(2012/08/08)
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- Iron(II) chloride catalyzed alkylation of propargyl ethers: Direct functionalization of an sp3 C-H bond adjacent to oxygen
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Iron(II) chloride catalyzed direct alkylation of sp3 C-H bond adjacent to oxygen in propargyl ethers has been accomplished by the use of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant under mild reaction conditions. The reaction proceeded smoothly with a variety of 1,3-diketones leading to -dicarbonyl ether in moderate yields. In the absence of 1,3-diketones, ynenones were produced by the use of iron(III) chloride and DDQ. Georg Thieme Verlag Stuttgart - New York.
- Xie, Yongju,Yu, Ming,Zhang, Yuhong
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supporting information; experimental part
p. 2803 - 2809
(2011/10/09)
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