- Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
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In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.
- Kuribara, Takahito,Nakajima, Masaya,Nemoto, Tetsuhiro
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supporting information
p. 2235 - 2239
(2020/03/13)
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- A simple synthesis of 5-(2-Aminophenyl)-1H-pyrazoles
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A four-step synthesis of 1-substituted 5-(2-aminophenyl)-1H-pyrazoles 5 as a novel type of histamine analogs and versatile building blocks for further transformations was developed. The synthesis starts from commercially available 2-nitroacetophenone (12), which is converted into the enamino ketone 13 as the key intermediate. Cyclization of the key intermediate 13 with monosubstituted hydrazines 14a-14l afforded the 5-(2-nitrophenyl)-1H-pyrazoles 17a-17l. Finally, catalytic hydrogenation of the nitro compounds 17a, 17c-17e, and 17g-17j furnished the title compounds 5a, 5c-5e, and 5g-5j, respectively, in good yields. As demonstrated by some further transformations, additional functionalization of compounds 17 and 5 is feasible, either by electrophilic substitution at C(4) of the pyrazole ring, or at the NH2 group. Copyright
- Janjic, Monika,Prebil, Rok,Groselj, Uros,Kralj, David,Malavasic, Crt,Golobic, Amalija,Stare, Katarina,Dahmann, Georg,Stanovnik, Branko,Svete, Jurij
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scheme or table
p. 1703 - 1717
(2011/10/31)
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- Synthesis, spectroscopic studies, and x-ray crystal structure of N-heteryliminophosphoranes
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N-[2-(α-Bromoacetyl)phenyl]imides (prepared in two steps from 2-aminoacetophenone) gave, upon treatment with sodium azide, fused azidoquinolines via an intramolecular cyclization. Reaction of the above azides with phosphines gave N-heteryliminophosphoranes. The IR, 1H-, 13C-, and 31P-NMR and MS spectra of these compounds as well as the x-ray crystal structure of two of them is reported.
- Alkhathlan,Al-Jaradah,Al-Farhan,Mousa
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p. 373 - 388
(2007/10/03)
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- A new route to quinolone and indole skeletones via ketone- and ester-imide cyclodehydration reactions
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Ketone-imide cyclodehydration reactions of aromatic succinimide and phthalimide (7, 8) have afforded quinolone acids (11, 12). Further transformation of the acids provided the corresponding esters (13, 14) and vinylogous urethanes (9, 10). Similarly, ester-imide cyclodehydration reactions of aromatic imide esters (19, 20) have afforded indole acids (23, 24).
- Kim, Guncheol,Keum, Gyochang
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p. 1979 - 1988
(2007/10/03)
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- Synthesis and spectroscopic studies of some novel quinoline derivatives
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An intramolecular Wittig reaction of some substituted aminoacetophenones was used for the synthesis of novel quinoline derivatives. In addition, the base induced cyclization of the aminoacetophenones was investigated. The IR and NMR spectra of the quinoline derivatives are reported.
- Alkhathlan
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p. 2659 - 2671
(2007/10/02)
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- Novel Approach to Pyrroloquinoline-1,5-diones
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The condensation of 2-aminoacetophenone with acid anhydrides is investigated.Different fused 4-quinolone derivatives were prepared in one step via this condensation.In addition different N-substituted imides were also obtained.
- AlKhathlan, Hamad Z.
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p. 1984 - 1996
(2007/10/02)
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