- Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds
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A photoelectrochemical strategy for the cross-dehydrogenative coupling of unactivated aliphatic hydrogen donors (e.g.alkanes) with benzothiazoles is reported. We used tetrabutylammonium decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochemistry scavenged the extra electrons.
- Capaldo, Luca,Quadri, Lorenzo L.,Merli, Daniele,Ravelli, Davide
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supporting information
p. 4424 - 4427
(2021/05/10)
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- Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines
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The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.
- Wu, Yue,Guo, Peng,Chen, Long,Duan, Weijie,Yang, Zengzhuan,Wang, Tao,Chen, Ting,Xiong, Fei
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supporting information
p. 3271 - 3274
(2021/04/07)
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- Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
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A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
- Mukhopadhyay, Sushobhan,Batra, Sanjay
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supporting information
p. 14622 - 14626
(2018/09/21)
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- Dual C-H activations of electron-deficient heteroarenes: Palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides
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The palladium-catalyzed, copper-promoted cross-dehydrogenative-coupling (CDC) of electron-deficient thiazoles with azine N-oxides through dual C-H activations was developed. It was found that copper(II) pivalate was an efficient dual-function reagent for the oxidative cross-coupling reactions, playing the roles of both an oxidant and a C-H bond activation promoter. This methodology provides a simple way to construct 2-thiazolyl pyridine moiety.
- Fu, Xiao-Pu,Xuan, Qing-Qing,Liu, Li,Wang, Dong,Chen, Yong-Jun,Li, Chao-Jun
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p. 4436 - 4444
(2013/06/26)
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- (3R)-3-Amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide as a potent dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
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Novel series of 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides and 3-amino-N-(4-aryltetrahydropyran-4-yl)butanamides were synthesized and evaluated as dipeptidyl peptidase IV (DPP-IV) inhibitors. Derivatives incorporating the 6-substituted benzothiazole group showed highly potent DPP-IV inhibitory activity. Oral administration of (3R)-3-amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide (12u) reduced blood glucose excursion in an oral glucose tolerance test.
- Nitta, Aiko,Fujii, Hideaki,Sakami, Satoshi,Nishimura, Yutaka,Ohyama, Tomofumi,Satoh, Mikiya,Nakaki, Junko,Satoh, Shiho,Inada, Chifumi,Kozono, Hideki,Kumagai, Hiroki,Shimamura, Masahiro,Fukazawa, Tominaga,Kawai, Hideki
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scheme or table
p. 5435 - 5438
(2009/05/30)
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- Syntheses of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines
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The condensation of α,β-unsaturated ketones with substituted o-aminothiophenols, obtained by reductive cleavage of the corresponding disulfides in the presence of triphenylphosphine, is an effective method for the synthesis of 2,4-diaryl-2,3-dihydro-1,5-b
- Katritzky,Rogovoy,Chassaing,Vvedensky,Forood,Flatt,Nakai
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p. 1655 - 1658
(2007/10/03)
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- Highly selective aldose reductase inhibitors. II. Optimization of the aryl part of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids
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Accumulation of intracellular sorbitol, the product of glucose reduction catalyzed by aldose reductase (AR) [EC 1.1.1.21], is thought to be the main culprit in the development of diabetic complications. A series of 3- arylalkyl-2,4,5-trioxoimidazolidine-1-acetic acids was prepared and tested for inhibitory activities towards AR and aldehyde reductase (ALR) [EC 1.1.1.2]. These derivatives showed strong inhibitory activity against AR without markedly inhibiting ALR. In particular, the compounds with 3- nitrophenyl, 4-chloro-3-nitrophenyl, and chloro-substituted benzothiazolyl groups as the aryl part showed powerful AR-inhibitory activity. The chloro- substituted benzothiazolyl compound showed an AR selectivity of more than 5000 fold.
- Kotani, Takayuki,Ishii, Akira,Nagaki, Yasuhiro,Toyomaki, Yoshio,Yago, Hisashi,Suehiro, Seishi,Okukado, Nobuhisa,Okamoto, Kaoru
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p. 297 - 304
(2007/10/03)
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