- Ruthenium-Catalyzed Alkylation of Cyclopropanols with Sulfoxonium Ylides via C-C Bond Cleavage: Formation of Diverse 1,5-Diketones
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A novel ruthenium-catalyzed alkylation of cyclopropanols with sulfoxonium ylides has been developed that affords diverse 1,5-diketones with good efficiency and broad substrate scope. To illustrate the synthetic applications of the obtained 1,5-diketones, aldol and cyclization reactions have been investigated. Preliminary mechanistic studies suggest that this process involves a sequential C C activation and carbene migratory insertion.
- Huang, Xin,Li, Jianglian,He, Hua,Yan, Kaichuan,Lai, Ruizhi,Luo, Yi,Guan, Mei,Wu, Yong
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p. 779 - 787
(2021/10/29)
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- Synthesis of 2-Arylphenol Derivatives through a One-Pot Suzuki-Miyaura Coupling/Dehydrogenative Aromatization Sequence with Pd/C Catalysis
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One-pot synthesis of 2-arylphenols starting from 2-iodo-2-cyclohexen-1-one and arylboronic acids through sequential Suzuki-Miyaura coupling/dehydrogenative aromatization with Pd/C catalysis has been developed. A range of arylboronic acids serve as substrates, including those containing electron-donating or electron-withdrawing groups. Additionally, one-pot synthesis of di- or trisubstituted phenols bearing a phenyl group at the ortho position are also generated by using 2-iodo-2-cyclohexen-1-one derivatives as substrate. In the present method, commercially available and easily removable Pd/C was employed as a catalyst without any ligands. The operationally simple procedure and accessible conditions were used to provide modified phenols as the sole product in moderate to high yields.
- Kikushima, Kotaro,Nishina, Yuta
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p. 5864 - 5868
(2015/09/15)
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- Zn(II)- or Rh(I)-catalyzed rearrangement of silylated [1,1'-Bi(cyclopropan) ]-2'-en-1-ols
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The rearrangement reactions of silylated alcohols bearing the highly strained structures of cyclopropene and cyclopropanol connected in adjacent positions have been studied under ZnI2- and Rh(I)-catalyzed conditions. The results show intriguing
- Zhang, Hang,Li, Changkun,Xie, Guojun,Wang, Bo,Zhang, Yan,Wang, Jianbo
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p. 6286 - 6293
(2014/07/21)
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- Agents for the treatment of overactive detrusor. VII. Synthesis and pharmacological properties of 2,3- and 3,4-diphenylcyclopentylamines, 2,3-diphenyl-2-cyclopentylamines, and related compounds
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As part of our search for new agents for the treatment of overactive detrusor, 2,3- and 3,4-diphenylcyclopentylamines (3), 2,3-diphenyl-2-cyclopentenylamines (4), and related compounds (5 and 18) were synthesized and evaluated for inhibitory activity (i.v.) against urinary bladder rhythmic contraction in rats. Among them, some compounds involving N-tert-butyl-2,3-diphenyl-2-cyclopentenylamine (4b) exhibited inhibitory activity against bladder contraction superior to that of terodiline (2). Mydriatic activity (i.v.) of compound 4b in rats, an index of its side effects due to antimuscarinic activity, was found to be relatively weak in comparison with its inhibitory activity against bladder contraction. The pharmacological profile of 4b was examined in comparisen with that of terodiline. Most of the objective amines (3, 4, 5) were synthesized by preparation of Schiff bases from the corresponding cyclic ketones (6, 7, 8) and amines in the presence of TiCl4 in CH2Cl2 and subsequent reduction with NaBH4 in the presence of MeOH in one pot (method A).
- Taniguchi,Tsubaki,Take,Okumura,Terai,Shiokawa
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p. 896 - 902
(2007/10/02)
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- Reaction of Alkynes with Cyclopropylcarbene-Chromium Complexes: A Versatile Cycloaddition Reaction for the Construction of Cyclopentenones
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The scope and limitations of the reaction between cyclopropylcarbene-chromium complexes and alkynes have been examined.A variety of cyclopropylcarbene complexes and alkynes have been employed in these studies.The reaction appears to be general for most simple alkynes, producing cyclopentenones.A mechanism has been proposed involving metallacyclobutene formation, electrocyclic ring opening, electrocyclic ring closure, CO insertion, alkene insertion, metallacyclopentene fragmentation and cyclopentadienone reduction.The presence of these intermediates has been inferred from the structure of products obtained when the reaction was conducted in acetonitrile instead of dioxane.A trapping experiment employing 1,6-heptadiyne supports the intermediacy of vinylcarbene or vinylketene complexes.
- Tumer, Seniz U.,Herndon, James W.,McMullen, Leonard A.
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p. 8394 - 8404
(2007/10/02)
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