- Microwave-assisted, solvent-free Bischler indole synthesis
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The solid-state reaction between anilines and phenacyl bromides in the presence of an equimolecular amount of sodium bicarbonate gives N-phenacylanilines. Microwave irradiation of mixtures of these compounds with anilinium bromides at 540 W for 45-60 s provides a mild, general, and environmentally friendly method for the synthesis of 2-arylindoles in 50-56% overall yields. A one-pot variation of the method, involving irradiation of 2:1 mixtures of anilines and phenacyl bromides, was also developed, allowing a simplified experimental procedure and leading to improved yields (52-75%). Georg Thieme Verlag Stuttgart.
- Sridharan, Vellaisamy,Perumal, Subbu,Avenda?o, Carmen,Menéndez, J. Carlos
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- Regioselective Synthesis of 2-Arylindoles via Palladium-Catalyzed Cyclization of Phenylglyoxal and 2-Anilinoacetophenones with Anilines
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A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.
- Benitez-Medina, G. Eliad,Ortiz-Soto, Sofía,Cabrera, Armando,Amézquita-Valencia, Manuel
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p. 3763 - 3770
(2019/06/24)
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- Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo
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A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.
- Dan, Wen-Jia,Tuong, Thi-Mai-Luong,Wang, Da-Cheng,Li, Ding,Zhang, An-Ling,Gao, Jin-Ming
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supporting information
p. 2861 - 2864
(2018/07/25)
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- Synthesis of (Z)-nitroalkene derivatives through oxidative dehydrogenation coupling of α-aminocarbonyl compounds with nitromethane by copper catalysis
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A novel copper-catalyzed cross-dehydrogenative coupling reaction of α-amino carbonyl compounds with nitromethane to synthesis of (Z)-nitroalkene derivatives has been established. (Z)-Nitroalkene derivatives are achieved through the cleavage of sp3 CsbndH bonds and formation of CsbndC double bond, with mild reaction conditions and excellent stereoselectivity.
- Zhu, Menghua,Chen, De,Zeng, Sheng,Xing, Chenhu,Deng, Wei,Xiang, Jiannan,Wang, Rui-Jia
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supporting information
p. 3214 - 3219
(2018/07/21)
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- Copper-catalyzed oxidative cross-coupling of α-aminocarbonyl compounds with primary amines toward 2-oxo-acetamidines
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A general and mild method for the construction of a carbon-nitrogen bond via copper-catalyzed oxidative cross-coupling of amines with α-aminocarbonyl compounds was achieved. Amines, either aliphatic primary amines, aromatic primary amines or secondary amines can be used as the starting materials. When R2 was different from R3, two isomers would be observed. Therefore, this reaction system has a broad substrate scope and provides a facile pathway for the synthesis of 2-oxo-acetamidines.
- Chen, Chuang,Zhu, Menghua,Jiang, Lihui,Zeng, Zebing,Yi, Niannian,Xiang, Jiannan
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supporting information
p. 8134 - 8139
(2017/10/10)
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- Iron-catalyzed direct α-arylation of α-amino carbonyl compounds with indoles
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A mild and general α-arylation of α-amino carbonyls with indoles catalyzed by Fe(ClO4)3 has been developed. C-H activation is smoothly fulfilled by using TBHP as the oxidant with good yields. Two hydrogen dissociations make this transformation more environmentally benign because of high atom efficiency.
- Zhang, Yan,Ni, Minjie,Feng, Bainian
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supporting information
p. 1550 - 1554
(2016/02/10)
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- One-Pot Metal-Free Cascade Synthesis of 2-(Perfluoroalkyl)pyrroles
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An efficient synthesis of 2-(perfluoroalkyl)pyrroles that employs a sequential one-pot three-component reaction between substituted ω-bromoacetophenones, anilines, and methyl perfluoroalk-2-ynoates has been developed. This transition-metal-free cascade pr
- Sun, Xuechun,Han, Jing,Chen, Jie,Deng, Hongmei,Shao, Min,Zhang, Hui,Cao, Weiguo
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supporting information
p. 7086 - 7090
(2015/11/16)
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- PREPARATION OF NEW THIOHYDROXAMIC ACID DERIVATIVES: SYNTHESIS OF SUBSTITUTED 1-HYDROXY-1,2-DIHYDROIMIDAZOLE-2-THIONES
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A general method for the synthesis of the title compounds is reported.The N-phenacylarylamines (11), prepared from the corresponding phenacyl bromides (9) and arylamines (10), give the thiono (or dithio) carbamates (12) on treatment with phenoxythionocarb
- Barton, Derek H. R.,Chern, Ching-Yu,Tachdjian, Catherine
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p. 793 - 806
(2007/10/02)
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