- Photoredox-Catalyzed Tandem Demethylation of N,N-Dimethyl Anilines Followed by Amidation with α-Keto or Alkynyl Carboxylic Acids
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We report herein, a biomimetic approach for highly selective monodemethylation of N,N-dimethyl anilines to generate secondary amines and subsequent coupling with α-ketocarboxylic acids or alkynyl carboxylic acids to form α-ketoamides or alkynamides respectively under visible light photoredox catalyst in a single operation. From the deuterium-labeling experiment, it was probed that demethylation is the slowest step in this tandem process. Whereas, control experiments and spectroscopic studies revealed that photoredox catalyst is also involved in the subsequent amidation step. The reaction proceeds smoothly at room temperature providing moderate to excellent yield of the coupling products. The amides have also been converted to a series of biologically active spiro compounds. (Figure presented.).
- Das, Pritha,Begam, Hasina Mamataj,Bhunia, Samir Kumar,Jana, Ranjan
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p. 4048 - 4054
(2019/07/19)
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- Multiple Aryne Insertions into Oxindoles: Synthesis of Bioactive 3,3-Diarylated Oxindoles and Dibenzo[b,e]azepin-6-ones
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An aryne insertion cascade reaction on oxindoles has been observed and constitutes a convenient one pot preparation of bioactive di- and triarylated oxindoles in good yields under mild conditions. A temperature controlled reaction switch enables ready access to dibenzo[b,e]azepin-6-one derivatives employing the same reaction regime. This tactic has been extended to a short synthesis of potent antiulcer agent darenzepine.
- Samineni, Ramesh,Bandi, Chandramohan Reddy C.,Srihari, Pabbaraja,Mehta, Goverdhan
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supporting information
p. 6184 - 6187
(2016/12/09)
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- Transition metal and base-free synthesis of 3,3-diaryl-2-oxindoles from 2,2,N-triarylacetamides
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A transition metal and base-free synthesis of 3,3-diaryl-2-oxindoles has been developed from 2,2,N-triarylacetamides in the presence of montmorillonite K-10 in 1,2-dichlorobenzene under O2 balloon atmosphere.
- Lim, Jin Woo,Kim, Ko Hoon,Moon, Hye Ran,Kim, Jae Nyoung
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supporting information
p. 784 - 787
(2016/02/03)
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- Transition-metal-free synthesis of oxindoles by potassium tert-butoxide-promoted intramolecular α-arylation
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Potassium tert-butoxide-mediated intramolecular α-arylations of fluoro- and chloro-substituted anilides provide oxindoles in DMF at 80 °C. In this manner, diversely substituted products have been obtained in moderate to high yields.
- Beyer, Astrid,Buendia, Julien,Bolm, Carsten
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p. 3948 - 3951
(2012/10/08)
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- 3-3-DI-SUBSTITUTED-OXINDOLES AS INHIBITORS OF TRANSLATION INITIATION
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Compositions and methods for inhibiting translation using 3-(5-tert-Butyl-2-Hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one and/or its derivatives are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using 3-(5-tert-butyl-2-hydroxy-phenyl)-3-phenyl-1,3-dihydro-indol-2-one and/or its derivatives are described.
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Page/Page column 32
(2008/06/13)
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- Preparation of 3,3-Diaryloxindoles by superacid-induced condensations of isatins and aromatics with a combinatorial approach
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3,3-Diaryloxidoles are prepared in high yields (62-99%) by reaction of isatin or substituted isatins with aromatics in triflic acid. The reaction shows a significant dependence on acid strength which suggests the formation of diprotonated, superelectrophi
- Klumpp, Douglas A.,Yeung, Ka Yeun,Prakash, G.K. Surya,Olah, George A.
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p. 4481 - 4484
(2007/10/03)
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- Heterocyclic 8?-Systems, 16 - Elimination Reactions of 2-Alkoxy-3-hydroxyindolines
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Thermolysis of 2-ethoxy-3-hydroxyindolines 1a - f affords oxindoles 3a - f as main products and the corresponding 3-indolinones 2a - f as by-products.The reaction course via indole 2,3-oxide intermediates is discussed.For this reason rearrangement reactio
- Beitzke, Bernhard,Schmidt, Richard R.
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p. 1726 - 1731
(2007/10/02)
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- ADDITION REACTION OF SULFUR DICHLORIDE TO FUNCTIONALIZED IMINES DIRECTED TOWARD HETEROCYCLIC SYNTHESIS
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Although it was shown that the reactions of sulfur dichloride (SCl2) with imines 1a-c or with the azine 14 gave rise to very unstable 1:1 adducts, 1-aza- and 2-azabutadienes, 5 and 10, reacted with SCl2 to afford the isothiazoles 6 and the thiazoles 11, respectively, in high yields.Addition of SCl2 to heterocumulenes was also studied and the ketenimines 16 and diphenylketene 27 gave 1:1 adducts which were applied to heterocyclic synthesis as bifunctional reagents.Addition of SCl2 to these compounds was investigated by monitoring the reactions by 13C nmr spectroscopy.
- Komatsu, Mitsuo,Harada, Nobuyuki,Kashiwagi, Hiroshi,Ohshiro, Yoshiki,Agawa, Toshio
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p. 119 - 134
(2007/10/02)
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