- Gold(I)-catalyzed furan-yne cyclizations involving 1,2-rearrangement: Efficient synthesis of functionalized 1-naphthols and its application to the synthesis of wailupemycin g
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Gold-catalyzed cascade cyclization/1,2-rearrangement of 1-(2-furanyl)phenyl propargyl alcohols has been developed, which provides a rapid and efficient access to multisubstituted 1-naphthols bearing an enal or enone moiety with high stereoselectivity. The (Z)- or (E)-stereochemistry can be easily controlled by choosing protected- or non-protected substrates. The utility of the methodology has been illustrated in the first total synthesis of wailupemycin G.
- Chen, Yifeng,Wang, Lu,Sun, Ning,Xie, Xin,Zhou, Xiaobo,Chen, Haoyi,Li, Yuxue,Liu, Yuanhong
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- Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement
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Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.
- Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun
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supporting information
p. 5506 - 5511
(2021/07/31)
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- Gold-catalyzed spirocyclization of furan-ynones and unexpected skeleton rearrangement of the resulting spirohydrofurans
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A gold-catalyzed cyclization of aniline-tethered furan-ynones has been developed. The reaction proceeds via trapping of the resulting stabilized cationic intermediate with an amide group leading to polycycles featured with a spiro-cyclohexadienonehydrofur
- Chen, Yulong,Xu, Wei,Xie, Xin,Pei, Miaomiao,Lu, Mingduo,Wang, Yaotong,Liu, Yuanhong
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supporting information
p. 1090 - 1095
(2021/02/01)
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- Metal-free synthesis of 2-aminonaphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles
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A facile metal-free synthesis of naphthalenes by intramolecular transannulation of 1-sulfonyl-4-(2-alkenylphenyl)-1,2,3-triazoles was realized. The in situ formed ketenimine was proposed as the key intermediate, and the desired 2-aminonaphthalenes were generated in up to 87% yield in refluxing 1,2-dichloroethane without any catalyst or additive.
- Xu, Ze-Feng,Yu, Xing,Yang, Dongdong,Li, Chuan-Ying
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supporting information
p. 3161 - 3164
(2017/04/21)
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- Based on 4 - phenyl -6 - (2, 2, 2 - trifluoro -1 - phenyl ethoxy) pyrimidine compound and its application method
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The present invention relates to compounds based on 4-phenyl-6-(2,2,2-trifluoro-1-phenyl ethoxy) pyrimidine and an application method thereof, particularly discloses compounds of formula I and compositions comprising the compounds, and the application method thereof in treatment, prevention and / or management of diseases or disorders.
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Paragraph 0342
(2017/08/25)
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- Bis(cyclopropenium)phosphines: Synthesis, Reactivity, and Applications
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A straightforward route for the preparation of a set of bis(cyclopropenium)-substituted phosphines is reported. Due to their dicationic nature, these ligands depict an excellent π-acceptor character. The effect of the ligand substituent pattern on the catalytic activity of the metal complexes thereof derived is also studied. Whereas sterically demanding biaryl groups directly attached to the phosphorus atom seem to facilitate elementary steps such as the product release from the catalyst, long chain dialkylamino groups on the cyclopropenium units maximize the catalysts solubility and, thus, allow the use of typical apolar solvents such as toluene. Importantly, all new ligands prepared can be easily handled in air. Finally, the impact of the newly prepared dicationic phosphines in hydroarylation reactions is demonstrated. In particular, their use in the synthesis of several naphtho[1,2-b]furanes and naturally occurring naphthalene derivatives such as Calanquinone C is reported.
- Mehler, Gerlinde,Linowski, Pawel,Carreras, Javier,Zanardi, Alessandro,Dube, Jonathan W.,Alcarazo, Manuel
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supporting information
p. 15320 - 15327
(2016/10/13)
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- Cycloaddition Reaction of Vinylphenylfurans and Dimethyl Acetylenedicarboxylate to [8 + 2] Isomers via Tandem [4 + 2]/Diradical Alkene-Alkene Coupling/[1,3]-H Shift Reactions: Experimental Exploration and DFT Understanding of Reaction Mechanisms
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An experimental test of designed [8 + 2] reaction of vinylphenylfuran and dimethyl acetylenedicarboxylate (DMAD) has been carried out, showing that the reaction gave unexpected addition products under different conditions. When the reaction was conducted under thermal conditions in toluene, expoxyphenanthrene, which was named as a [8 + 2] isomer, was generated. The scope of this reaction has been investigated in the present study. In addition, experiments and DFT calculations have been conducted to investigate how the reaction between vinylphenylfuran and DMAD took place. Surprisingly, the reaction did not involve the expected [8 + 2] intermediate, o-quinodimethane. Instead, the reaction starts from intermolecular Diels-Alder reactions between DMAD and the furan moiety of vinylphenylfuran, followed by unexpected intramolecular alkene-alkene coupling. This step generates a diradical species, which then undergoes [1,3]-H shift to give the experimentally observed expoxyphenanthrene. DFT calculations revealed that, the [8 + 2] cycloadduct cannot be obtained because the [1,5]-H shift process from the [1,5]-vinyl shift intermediate is disfavored kinetically compared to the [1,3]-H shift to the [8 + 2] isomer.
- Chen, Kai,Wu, Feng,Ye, Lijuan,Tian, Zi-You,Yu, Zhi-Xiang,Zhu, Shifa
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supporting information
p. 8155 - 8168
(2016/09/28)
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- Photoassisted diversity-oriented synthesis: Accessing 2,6-epoxyazocane (oxamorphan) cores
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The modular synthesis of photoprecursors and their photoinduced cyclization into substituted 1-benzazocanes of two distinct topologies is described. The key step producing an extended polyheterocyclic system involves the photogeneration of azaxylylenes and their subsequent intramolecular cycloaddition with furan-containing pendants tethered either via the aniline nitrogen or through the carbonyl group containing arm. The primary photoproducts-secondary or tertiary anilines which are not acylated at the nitrogen atom-undergo facile acid-catalyzed or spontaneous ring-opening-ring-closing rearrangement to yield fused polyheterocyclic structures possessing a 2,6-epoxyazocane (or oxamorphan) core.
- Mukhina, Olga A.,Kumar, N. N. Bhuvan,Cowger, Teresa M.,Kutateladze, Andrei G.
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p. 10956 - 10971
(2015/01/08)
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- Intramolecular gold(III) catalysed Diels-Alder reaction of 1-(2-furyl)-hex-1-en-5-yn-3-ol derivatives: A short and generalised route for the synthesis of hydroxyphenanthrene derivatives
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Gold(III) catalysed intramolecular Diels-Alder reaction of various 1-(2-furyl)-hex-1-en-5-yn-3-ol derivatives has been studied to synthesise hydroxyphenanthrenes and other polynuclear aromatic hydroxyl compounds. The required precursors were synthesised by indium mediated propargylation of suitable β-furyl-α,β-unsaturated aldehydes.
- Samanta, Khokan,Kar, Gandhi K.,Sarkar, Achintya K.
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supporting information; experimental part
p. 1376 - 1379
(2012/04/04)
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- Modulation of peripheral serotonin levels by novel tryptophan hydroxylase inhibitors for the potential treatment of functional gastrointestinal disorders
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The discovery of a novel class of peripheral tryptophan hydroxylase (TPH) inhibitors is described. This class of TPH inhibitors exhibits excellent potency in in vitro biochemical and cell-based assays, and it selectively reduces serotonin levels in the murine intestine after oral administration without affecting levels in the brain. These TPH1 inhibitors may provide novel treatments for gastrointestinal disorders associated with dysregulation of the serotonergic system, such as chemotherapy-induced emesis and irritable bowel syndrome.
- Shi, Zhi-Cai,Devasagayaraj, Arokiasamy,Gu, Kunjian,Jin, Haihong,Marinelli, Brett,Samala, Lakshman,Scott, Sheldon,Stouch, Terry,Tunoori, Ashok,Wang, Ying,Zang, Yi,Zhang, Chengmin,Kimball, S. David,Main, Alan J.,Sun, Weimei,Yang, Qi,Nouraldeen, Amr,Yu, Xiang-Qing,Buxton, Eric,Patel, Shiv,Nguyen, Nghi,Swaffield, Jon,Powell, David R.,Wilson, Alan,Liu, Qingyun
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supporting information; experimental part
p. 3684 - 3687
(2009/04/06)
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- 4-PHENYL-6-(2,2,2-TRIFLUORO-1-PHENYLETHOXY)PYRIMIDINE-BASED COMPOUNDS AND METHODS OF THEIR USE
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Compounds of formula I are disclosed, as well as compositions comprising them and methods of their use to treat, prevent and/or manage diseases and disorders:
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Page/Page column 29-30
(2008/12/06)
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- Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls
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The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields
- Demir, Ayhan S.,Reis, Oemer,Emrullahoglu, Mustafa
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p. 578 - 580
(2007/10/03)
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- Novel cyclic amide derivatives
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Novel compounds represented by the following formula (I) that act as a ligand to sigma receptor/binding cite and a medicament comprising the same as an active ingredient: wherein X represents an alkyl group, an aryl group, a heterocyclic group or the like; Q represents a group represented by —CH2—, —CO—, —O—, —CH(OR7)— or the like wherein R7 represents a hydrogen atom, an alkyl group or the like; n represents an integer of from 0 to 5; R1 and R2 each represent a hydrogen atom, an alkyl group or the like; B represents either of the following groups: wherein R3, R4, R5, and R6 each represent a hydrogen atom, a halogen atom, an alkoxyl group or the like; m represents 1 or 2; and the ring of: represents an aromatic heterocyclic ring.
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