34761-56-3Relevant academic research and scientific papers
Halogen-Substituted Allenyl Ketones through Ring Opening of Nonstrained Cycloalkanols
Wu, Penglin,Ma, Shengming
supporting information, p. 2533 - 2537 (2021/04/13)
An efficient synthesis of halogen-substituted allenyl ketones via Ag-catalyzed oxidative ring opening of allenyl cyclic alcohols under mild reaction conditions has been achieved. The reaction features a wide substrate scope and excellent regioselectivity. The synthetic potential of the products has been demonstrated by their conversion to stereodefined alkenes and heterocyclic compounds.
SUBSTITUTED IMIDAZOLECARBOXYLATE DERIVATIVES AND THE USE THEREOF
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Paragraph 0847; 0850-0851; 0945-0946, (2020/12/08)
A compound is shown in formula (I). The derivatives of the compound include a stereoisomer, a pharmaceutically acceptable salt, a solvate, a prodrug, a metabolite, a deuterated derivative. The compound is a structurally novel substituted imidazole formate derivative. Substituted imidazole formate derivatives are used in preparing a drug with sedative, hypnotic and/or anesthetic effects, as well as a drug that can control the state of epilepsy. The compound has a good inhibitory effect on the central nervous system, and provides a new option for clinical screening of and/or preparation of a drug with sedative, hypnotic and/or anesthetic effects and controlling the state of epilepsy.
Synthesis of Functionalized 1,3-Butadienes via Pd-Catalyzed Cross-Couplings of Substituted Allenic Esters in Water at Room Temperature
Lippincott, Daniel J.,Linstadt, Roscoe T. H.,Maser, Michael R.,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 4719 - 4722 (2018/08/23)
An environmentally responsible, mild method for the synthesis of functionalized 1,3-butadienes is presented. It utilizes allenic esters of varying substitution patterns, as well as a wide range of boron-based nucleophiles under palladium catalysis, generating sp-sp2, sp2-sp2, and sp2-sp3 bonds. Functional group tolerance measured via robustness screening, along with room temperature and aqueous reaction conditions highlight the methodology's breadth and potential utility in synthesis.
Azaphilic versus Carbophilic Coupling at C=N Bonds: Key Steps in Titanium-Assisted Multicomponent Reactions
Roth, Torsten,Wadepohl, Hubert,Clot, Eric,Gade, Lutz H.
supporting information, p. 18730 - 18738 (2016/01/25)
Consecutive C- and N-arylation of N-heterocyclic nitriles is mediated by titanium(IV) alkoxides. The carbo- and azaphilic arylation step may be separated by choosing the order in which the two equivalents of aryl transfer reagent are added. In the course of this transformation, the ancillary N-heterocycle acts as both a directing anchor group and electron reservoir. In the selectivity-determining step, the selectivity is governed by a choice between (direct) C- and Ti-arylation; the latter opens up a reaction pathway that allows further migration to the nitrogen atom. The isolation of metal-containing aggregates from the reaction mixture and computational studies gave insights into the reaction mechanism. Subsequently, a multicomponent one-pot protocol was devised to rapidly access complex quaternary carbon centers.
Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate
Yamashita, Yasuhiro,Cui, Yi,Xie, Peizhong,Kobayashi, Shu
supporting information, p. 6042 - 6045 (2016/01/09)
Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.
Rhodium-catalyzed chemo-, regio-, and enantioselective addition of 2-pyridones to terminal allenes
Li, Changkun,K?hny, Matthias,Breit, Bernhard
supporting information, p. 13780 - 13784 (2015/02/05)
A rhodium-catalyzed chemo-, regio-, and enantio-selective addition of 2-pyridones to terminal allenes to give branched N-allyl 2-pyridones is reported. Preliminary mechanistic studies support the hypothesis that the reaction was initiated from the more acidic 2-hydroxypyridine form, and the initial kinetic O-allylation product was finally converted into the thermodynamically more stable N-allyl 2-pyridones.
CuI-catalyzed synthesis of functionalized terminal allenes from 1-alkynes
Luo, Hongwen,Ma, Shengming
, p. 3041 - 3048 (2013/06/27)
Relative to our original protocol that uses CuI (0.5 equiv.), paraformaldehyde (2.5 equiv.), and dicyclohexylamine (1.8 equiv.), a facile and efficient protocol for the gram-scale synthesis of functionalized terminal allenes by using CuI (7.5-10 mol-%), p
A general approach to terminal allenols
Kuang, Jinqiang,Xie, Xi,Ma, Shengming
supporting information, p. 592 - 595 (2013/04/10)
We have demonstrated a very general method for the preparation of essentially any terminal 2,3-allenol from the corresponding alkynols, which may be easily available from propargylic alcohols by alkylation, or from terminal alkynes by deprotonation and 1,
Synthesis of allenes via CuBr-catalyzed homologation of alk-1-ynes accelerated by microwave
Nakamura, Hiroyuki,Sugiishi, Tsuyuka,Tanaka, Yuko
scheme or table, p. 7230 - 7233 (2009/04/14)
CuBr-catalyzed homologation of alk-1-ynes 1 with paraformaldehyde and N,N-diisopropylamine (or N,N-dicyclohexylamine) was accelerated by microwave irradiation at 150 °C to afford the corresponding allenes 2 in good to high yields in 1-10 min. Bisalkynes 5
Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl- 5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols
Cheng, Xin,Jiang, Xuefeng,Yu, Yihua,Ma, Shengming
supporting information; experimental part, p. 8960 - 8965 (2009/04/11)
(Chemical Equation Presented) A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of γ-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.
