- Flow hydrodediazoniation of aromatic heterocycles
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Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles, confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimised to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines, to be deaminated in good yield using a purely organic-soluble system.
- R?der, Liesa,Nicholls, Alexander J.,Baxendale, Ian R.
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- Synthesis of diaryl ketones through oxidative cleavage of the C-C double bonds in N -Sulfonyl enamides
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An oxidative cleavage of a C-C double bond is developed from the photochemical [2+2]-cycloaddition of diaryl N-tosyl enamides, aryl heteroaryl N-tosyl enamides, and N-tosyl cyclic enamides with singlet molecular oxygen, followed by a ring-opening reaction mediated by Cs2CO3 under air and sunlight without the use of photosesitizer, producing symmetrical and unsymmetrical diaryl, heterodiaryl, and cyclic ketones in good to excellent yields. Moreover, the oxidative cleavage of C-C triple bonds from 1-alkynes is demonstrated for the synthesis of symmetrical and unsymmetrical ketones from the Cu-catalyzed [3+2]-cycloaddition, Rh-catalyzed alkoxyarylation, photooxygenation, and ring-opening reaction in one-pot. Because the synthesis of the symmetrical and unsymmetrical diaryl and/or heterodiaryl ketones bearing an electron-donating group is not easy, the present method is notable.
- Kim, Hyunseok,Park, Sangjune,Baek, Yonghyeon,Um, Kyusik,Han, Gi Uk,Jeon, Da-Hye,Han, Sang Hoon,Lee, Phil Ho
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p. 3486 - 3496
(2018/04/14)
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- Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents
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The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.
- Huang, Pei-Qiang,Chen, Hang
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supporting information
p. 12584 - 12587
(2017/11/30)
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- Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids
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A nickel-based catalyst was employed in the cross-coupling of carboxylic anhydrides with arylboronic acids, and the reaction was carried out under mild conditions. This new protocol provides an efficient, cheap and convenient alternative to synthesizing aromatic ketones.
- Chen, Qiang,Fan, Xin-Heng,Zhang, Li-Peng,Yang, Lian-Ming
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p. 53885 - 53890
(2015/01/16)
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- 3-(diheteroarylmethylene)-8-azabicyclo[3.2.1]octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1]octane derivatives
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This invention is directed to 3-(diheteroarylmethylene)-8-azabicyclo[3.2.1] octane and 3-((aryl)(heteroaryl)methylene)-8-azabicyclo[3.2.1] octane derivatives useful as δ-opioid, μ-opioid, or δ-opioid and μ-opioid receptor receptor modulators. Depending on
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Page/Page column 19
(2010/02/13)
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- 4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors
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A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potentia
- Hartman,Halczenko,Smith,Sugrue,Mallorga,Michelson,Randall,Schwam,Sondey
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p. 3822 - 3831
(2007/10/02)
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- 4-Benzylthiophene (or furan)-2-sulfonamides as antiglaucoma agents
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Thiophene (or furan)-2-sulfonamides with a 4-benzyl substituent are effective in the treatment of elevated intraocular pressure and glaucoma following topical ocular administration.
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- 4-(benzoyl)thiophene(or furan)-sulfonamide and derivatives thereof for the topical treatment of elevated intraocular pressures
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4-(benzoyl)thiophene(or furan)-2-sulfonamide and derivatives thereof are useful for the topical treatment of elevated intraocular pressure.
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