- Phosphine-Catalyzed Synthesis of Chiral N-Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling
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Phosphine-catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2,5-dihydro-1H-pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines.
- Lorton, Charlotte,Saleh, Nidal,Voituriez, Arnaud
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supporting information
p. 3340 - 3344
(2021/06/26)
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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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- Iodine monobromide catalysed regioselective synthesis of 3-arylquinolines from α-aminoacetophenones and: Trans -β-nitrostyrenes
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A simple and efficient method for regioselective synthesis of 3-arylquinolines is described from α-aminoacetophenones and trans-β-nitrostyrenes using 20 mol% iodine monobromide as a catalyst in acetonitrile solvent at 80 °C. The present method involves tandem reaction of α-aminoacetophenones and trans-β-nitrostyrenes, formation of two new C-C bonds and cleavage of one C-C bond in a single step. The salient features of the protocol are metal- and oxidant-free reaction conditions, broad substrate scope, and good yields.
- Gattu, Radhakrishna,Mondal, Santa,Ali, Saghir,Khan, Abu T.
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supporting information
p. 347 - 353
(2019/01/10)
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- A one-pot and three-component synthetic approach for the preparation of asymmetric and multi-substituted 1,4-dihydropyrazines
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An efficient, one-pot and three-component synthesis of a new series of 2-acyl-3,4,6-triaryl-1,4-dihydropyrazines is described. This two-step strategy involves treatment of phenacyl bromides and anilines to give the nucleophilic substitution intermediate f
- Peytam, Fariba,Adib, Mehdi,Shourgeshty, Reihaneh,Rahmanian-Jazi, Mahmoud,Jahani, Mehdi,Larijani, Bagher,Mahdavi, Mohammad
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supporting information
(2019/11/11)
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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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p. 8134 - 8139
(2017/10/10)
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- CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
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Paragraph 000384; 000386
(2018/01/17)
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- Sequential One-Pot Synthesis of Imidazoles and 2H-Imidazolones from β-Ketoamines, Acylating Agents and Ammonium Acetate
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An efficient, practical, straight forward, and transition metal-free three-component synthesis of diversely substituted imidazoles and 2H-imidazolones from β-ketoamines, acylating agents, and ammonium acetate has been described herein. This approach invol
- Jalani, Hitesh B.,Venkateswararao, Eeda,Manickam, Manoj,Jung, Sang-Hun
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supporting information
p. 1966 - 1970
(2016/12/16)
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- Synthesis of Multiple-Substituted Pyrroles via Gold(I)-Catalyzed Hydroamination/Cyclization Cascade
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A gold-catalyzed cascade hydroamination/cyclization reaction of α-amino ketones with alkynes to form substituted pyrroles has been developed. The method offers several advantages such as high regioselectivity with the tested cases, wide functional group tolerance, and easily accessible starting materials. The synthetic utility of the obtained pyrrole products was demonstrated by their efficient transformations to 2-vinylated pyrroles via gold-catalyzed intermolecular hydroarylation.
- Li, Xiangdong,Chen, Ming,Xie, Xin,Sun, Ning,Li, Shi,Liu, Yuanhong
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supporting information
p. 2984 - 2987
(2015/06/30)
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- New efficient synthesis of 1,4-benzodiazepin-5-ones by catalytic aza-Wittig reaction
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1,4-Benzodiazepin-5-ones were synthesized in 71-89% yields from 2-isocyanato-N-(2-oxoalkyl)benzamides via a new catalytic intramolecular aza-Wittig reaction. Starting from easily accessible phthalic anhydride and α-arylamino ketones, the corresponding 2-{[(2-oxoalkyl)amino]carbonyl}benzoic acids underwent sequential formation of the acid azide and Curtis rearrangement to give 2-isocyanato-N-(2-oxoalkyl)benzamides that were reacted directly to give the final 2,4-diaryl-3,4-dihydro-5H-1,4-benzodiazepin-5-ones and 4-aryl-2-tert-butyl-3,4-dihydro-5H-1,4-benzodiazepin-5-ones.
- Wang, Long,Qin, Ru-Qing,Yan, Hong-Ye,Ding, Ming-Wu
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p. 3522 - 3528
(2015/11/17)
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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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- Synthesis, Characterization, and Antibacterial Activity of Some Novel Substituted Imidazole Derivatives via One-pot Three-Component
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A simple and highly efficient one-pot, three-component synthesis of novel substituted imidazole derivatives has been reported by the reaction of 3-(2-bromoacetyl)-2H-chromen-2-one, ammonium thiocyanate, and phenacyl aniline in the presence of acetic acid
- Ramagiri, Raj Kumar,Thupurani, Murali Krishna,Vedula, Rajeswar Rao
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p. 1713 - 1717
(2015/11/09)
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- New compounds for inhibiting differentiation of osteoclast and pharmaceutical composition comprising thereof
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New compounds and pharmaceutical compositions comprising active ingredients having inhibition effects on osteoclast differentiation are provided. The pharmaceutical compositions comprising the new compounds can be used as medicines for treating metabolic bone diseases such as bone metastatic cancer, solid cancer bone metastasis, musculoskeletal complication by solid cancer bone metastasis, hypercalcemia by malignant tumor, multiple myeloma, primary bone tumor, osteoporosis, rheumatoid arthritis, osteoarthritis, periodontal disease, inflammatory resorption of alveolar bone, inflammatory resorption of bone, and Paget's disease.
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Paragraph 0246; 0247
(2014/02/16)
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- Synthesis of optically active β-amino alcohols by asymmetric transfer hydrogenation of α-amino ketones
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A number of optically active amino alcohols were synthesized by direct asymmetric transfer hydrogenation of the corresponding amino ketones with good-to-high enantiomeric excesses (up to 95%) and excellent yields (up to 93%). When the range of substrates was broadened to include α-sulfonamido ketones or α-keto sulfones, the corresponding products were obtained with 100% enantiomeric excesses. The absolute configuration of (1R)-2-[(4- chlorophenyl) amino]-1-(4-methoxyphenyl) ethanol was confirmed by X-ray crystal structure analysis. Georg Thieme Verlag Stuttgart.
- Xu, Zhou,Zhu, Songlei,Liu, Yongmin,He, Ling,Geng, Zhicong,Zhang, Yawen
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scheme or table
p. 811 - 817
(2010/10/01)
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- 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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- A rapid and direct access to symmetrical/unsymmetrical 3,4-diarylmaleimides and pyrrolin-2-ones
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1,8-Diazabicyclo[5.4.0]undec-7ene (DBU) facilitated the oxidative cyclization of phenacyl amide in the presence of atmospheric oxygen under environmentally friendly conditions. The reaction has been studied under various conditions and a plausible mechani
- Pal, Manojit,Swamy, Nalivela Kumara,Hameed, P. Shahul,Padakanti, Srinivas,Yeleswarapu, Koteswar Rao
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p. 3987 - 3997
(2007/10/03)
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- Photochemistry of N-heterocycles. 7: Light induced reductive ring contractions of sixmembered cyclic iminium ions
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Photochemically induced reductive ring contractions, previously observed for 2,5-dihydro-1,2,4-triazines, have also been verified for 1,4-dihydropyrimidines 2a,b, the dihydro-1,2,4,5-tetrazine 9, and dihydro-1,3,5-triazines 11a,b giving rise to fivemembered fully unsaturated heterocycles (pyrroles 4a,b, imidazoles 13a,b, and triazole 10, respectively). The 1,4-dihydropyrazines 15a-j tend to decompose in acidified 2-propanol in the dark, but on irradiation they also undergo reductive ring contraction furnishing solely the 1,2,5-triarylpyrroles 16a-d rather than the (a priori also possible) isomeric 1,3,4-triarylpyrroles 17a-d. In contrast, the 3,6-diphenylpyrid-azine 18 gives the 4-isopropyl-analogue 19 in low yield upon irradiation in hydrogen chloride saturated 2-propanol. Wiley-VCH Verlag GmbH, 2000.
- Nagy, Jozsef,Madarasz, Zoltan,Rapp, Rudolf,Szoelloesy, Aron,Nyitrai, Jozsef,Doepp, Dietrich
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p. 281 - 290
(2007/10/03)
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- A convenient synthesis of α-anilinoacetophenones using hypervalent iodine
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Hypervalent iodine oxidation of acetophenones (1) with benzene, followed by treatment with appropriate aniline, provides a new, convenient and useful route to the synthesis of α-anilinoacetophenones (3a-h).
- Prakash, Om,Rani, Neena,Goyal, Seema
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p. 349 - 350
(2007/10/02)
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- Nucleophilic Substitution Reactions of Phenacyl Benzenesulphonates with Anilines in Methanol-Acetonitrile Mixtures
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The nucleophilic substitution reactions of phenacyl benzenesulphonates with anilines in methanol-acetonitrile have been studied.A stronger nucleophile was found to cause less bond cleavage, while a better leaving group led to less bond formation, in compl
- Lee, Ikchoon,Shim, Chang Sub,Chung, Soo Young,Lee, Hai Whang
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p. 975 - 982
(2007/10/02)
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