- One pot synthesis of α-N-heteroaryl ketone derivatives from aryl ketones using aqueous NaICl2
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A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.
- Ghodse, Shrikant M.,Hatvate, Navnath T.,Telvekar, Vikas N.
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supporting information
(2021/12/08)
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- Au(I)-Catalyzed Hydration of 1-Iodoalkynes Leading to α-Iodoketones
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A catalytic protocol for the Au(I)-catalyzed hydration of 1-iodoalkynes is disclosed. The use of Au(I)–NHC catalyst enabled the straightforward synthesis of a variety of α-iodomethyl ketones in good to excellent yields. The utility of this simple method is further highlighted by showcasing iodination/hydration and hydration/oxidation sequential protocols leading to the construction of molecular complexity.
- Cazin, Catherine S. J.,Gómez-Herrera, Alberto,Hashim, Ishfaq Ibni,Nahra, Fady,Porré, Marre
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supporting information
p. 6790 - 6794
(2020/11/23)
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- Solvent-Free Synthesis of α-Amino Ketones from α-Hydroxyl Ketones via A Novel Tandem Reaction Sequence Based on Heyns Rearrangement
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Heyns rearrangement have been famous for carbohydrate chemists for several decades. However, this reaction was underrated as a useful method for synthetic chemists due to preparative shortcomings. Herein we developed an efficient method for the synthesis of pharmaceutically important α-amino ketones from readily available α-hydroxy ketones and secondary amines through a tandem reaction sequence based on Heyns rearrangement. The reaction smoothly proceeded by using catalytic PTSA as catalyst without solvent. Primary and secondary α-hydroxy ketones were readily used and regioselectively afforded the correspondingly α-amino ketones with moderate yield.
- Li, Ling-Yu,Zeng, Qing-Le,Li, Guang-Xun,Tang, Zhuo
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supporting information
p. 694 - 699
(2019/03/26)
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- Electrochemical synthesis of α-enaminones from aryl ketones
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A novel approach to realize the synthesis of α-enaminones via an electrochemical oxidation was developed under mild conditions. This methodology opens up a simple and efficient strategy for the synthesis of α-enaminone derivatives in good yields. Accordin
- Li, Yanan,Gao, Huihui,Zhang, Zhenlei,Qian, Peng,Bi, Meixiang,Zha, Zhenggen,Wang, Zhiyong
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p. 8600 - 8603
(2016/07/13)
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- One pot rhodium catalysed three component dehydrogenation route to fused and spiro-heterocycles
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A three component rhodium-catalysed dehydrogenation reaction has been used for the synthesis of fused and spiro-heterocycles. The reaction proceeds in good yields with the formation of three new bonds and four stereocentres.
- Allison, Matthew,Sridharan, Visuvanathar
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supporting information
p. 6551 - 6555
(2015/11/09)
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- Direct use of formamides as amino group sources via C-N bond cleavage: A catalytic oxidative synthesis of α-ketoamides from acetophenones and formamides under metal-free conditions
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An efficient and direct use of formamides as amino group sources for the synthesis of α-ketoamides was developed under metal-free conditions. The reaction was based on the oxidative coupling of acetophenones with formamides and generated the desired products in good yields in the presence of t-BuOOH/I2/PhCO2H.
- Zhao, Qiong,Miao, Tao,Zhang, Xiaobin,Zhou, Wei,Wang, Lei
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p. 1867 - 1873
(2013/04/10)
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- TBHP/I2-promoted oxidative coupling of acetophenones with amines at room temperature under metal-free and solvent-free conditions for the synthesis of α-ketoamides
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A novel and efficient TBHP/I2-promoted oxidative coupling reaction of acetophenones with amines for the synthesis of α-ketoamides has been developed. The reactions proceeded smoothly at room temperature under metal-free and solvent-free conditions and generated the corresponding products in good yields.
- Zhang, Xiaobin,Wang, Lei
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scheme or table
p. 2141 - 2145
(2012/09/10)
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- Asymmetric synthesis of β-dialkylamino alcohols by transfer hydrogenation of α-dialkylamino ketones
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Transfer hydrogenation of representative aryl and heteroaryl dialkylaminomethyl ketones with formic acid-triethylamine, catalyzed by RuCl[(R,R)-TsDPEN](η-p-cymene), produces the corresponding β-dialkylamino alcohols, 97-99% ee, in 50-73% yields. Asymmetric synthesis of (R)-macromerine, 98% ee, the cactus Coryphantha macromeris alkaloid, is also described.
- Kosmalski, Tomasz,Wojtczak, Andrzej,Zaidlewicz, Marek
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experimental part
p. 1138 - 1143
(2009/09/27)
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- Novel N,S-phenacyl protecting group and its application for peptide synthesis
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The phenacyl group can be introduced onto amino and thio groups by N,S-alkylation reactions. Conversely, these groups are removed rapidly by employing magnesium in acetic acid. This protecting group was successfully applied to a short peptide synthesis of Boc-L-Cys-Gly-OMe. Georg Thieme Verlag Stuttgart.
- Tang, Guo,Ji, Tao,Hu, An-Fu,Zhao, Yu-Fen
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experimental part
p. 1907 - 1909
(2009/04/11)
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- Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones
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LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six α-aminophenones 4-9 into the corresponding optically active β-aminoalcohols 10-15 whose ee's were in the range of 40-97% after chroma
- Brown, Eric,Leze, Antoine,Touet, Joel
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p. 2029 - 2040
(2007/10/03)
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- Hypolipidemic effects of α, β, and γ-alkylaminophenone analogs in rodents
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A number of N-substituted β-alkylaminophenone derivatives including two (α- and two γ-alkylaminophenone analogs were synthesized and investigated for hypolipidemic activity in mice at 8 mg/kg/day ip. Most of these analogs were found to be significantly more active than lovastatin and clofibrate. N-Phenylpiperazinopropiophenone 16 was one of the best derivatives, lowering serum cholesterol levels 41% and serum triglyceride levels 48% after 16 days of drug administration in CF1 mice. In Sprague-Dawley rats, N-phenylpiperazinopropiophenone at 8 mg/kg/day orally also demonstrated more potent hypolipidemic activity than clofibrate, gemfibrozil, and lovastatin at their therapeutic dosage. It significantly reduced tissue cholesterol and triglyceride levels in the aorta wall tissue and lowered the cholesterol and triglyceride levels in chylomicron, very low density lipid (VLDL) and low density lipid (LDL) fractions, while it significantly elevated the cholesterol levels in high density lipid (HDL) fraction. This compound also proved to be active in lowering both cholesterol and triglyceride levels in hyperlipidemic mice and rats induced with atherogenic diet. In vitro liver acetyl coenzyme A (CoA) synthetase, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase, acyl CoA cholesterol acyl transferase (ACAT), sn-glycerol-3-phosphate acyltransferase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase activities were significantly inhibited by N-phenylpiperazinopropiophenone from 25 to 100 μM.
- Huang,Hall
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p. 281 - 290
(2007/10/03)
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- Synthesis, X-ray Structure and Reactions of (2-Oxoalkyl)triarylbismuthonium Salts
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Treatment of triarylbismuth difluorides 1 with silyl enol ethers 2 in the presence of boron trifluoride-diethyl ether or trimethylsilyl trifluoromethanesulfonate (triflate) gave (2-oxoalkyl)triarylbismuthonium tetrafluoroborates 3 and triflates 4 in good yields.A similar reaction of the difluorides 1 with hexamethyldisiloxane in the presence of the latter acid reagent led to the formation of oxybis(triarylbismuth) ditriflates 5.X-Ray crystallographic analyses of compounds 3a, 4a and 5a showed that the first two onium salts have a distorted tetrahedral geometry and the last, a μ-oxo type compound, has a distorted trigonal bipyramidal geometry around the bismuth centre.The stability of these bismuthonium salts may reasonably be attributed to the intramolecular coordinative interaction between the bismuth and oxygen atoms and also low nucleophilicity of the counter ions employed.The bismuthonium salt 3f readily underwent onium exchange with the phosphine 6 and the sulfide 9 to afford the corresponding phosphonium and sulfonium salts 7 and 10.The salts 3 and 4 also underwent coupling with a variety of nucleophiles such as the enolate 11, piperidine 13, the phenoxides 15, the thiolates 17, the sulfinate 19 and the halides 21 to afford the corresponding α-substituted ketones 12, 14, 16, 18, 20 and 22 in moderate to good yields, together with a good recovery of triphenylbismuthine 8.
- Matano, Yoshihiro,Azuma, Nagao,Suzuki, Hitomi
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p. 1739 - 1748
(2007/10/02)
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- Boranes in Synthesis. 2. Asymmetric Synthesis of β-Amino Alcohols. A Facile Conversion of 2-Amino Acetophenones to the Corresponding β-Amino Alcohols in High Enantiomeric Purity
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The asymmetric reduction of 2-amino acetophenones with Ipc2BH or Ipc2BCl at -78 deg C, yields the corresponding β-amino alcohols in good to excellent yields.Although only modest (12-45percent ee) enantiomeric excesses were obtained with Ipc2BH, 75-99perce
- Beardsley, David A.,Fisher, Gary B.,Goralski, Christian T.,Nicholson, Lawrence W.,Singaram, Bakthan
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p. 1511 - 1514
(2007/10/02)
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- Lewis Acid Complexed Heteroatom Carbanions; A New Concept for α-Metallation of Tertiary Amines
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BF3 complexes of typical benzylic, allylic and saturated N-methyl tertiary amines were α-lithiated, with lithium tetramethylpiperidide (LTMP) or sec-butyllithium, and were treated with electrophiles.
- Kessar, Satinder V.,Singh, Paramjit,Vohra, Rahul,Kaur, Nachhattar Pal,Singh, Kamal Nain
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p. 568 - 570
(2007/10/02)
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- CATALYSIS IN THE FORMATION OF α-AMINO KETONES
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The kinetics of the reaction of α-halogenoacetophenones with piperidine and N-methylpiperidine in cyclohexane at 30 deg C were investigated.The autocatalytic nature of these reactions is due to the formation of catalitically active acidic products from degradation of the α-aminoacetophenone in the reaction system.The catalytic effect of additions of acetic acid and phenol on the rate of the reactions of α-halogenoacetophenone with piperidine and N-methylpiperidine is described quantitatively.Catalysis by acetic acid in the reactions of α-halogenoacetophenones with piperidine has a bifunctional mechanism.
- Popov, A. F.,Anikeev, A. V.
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p. 939 - 944
(2007/10/02)
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- Silicon Polonovski Reaction. Formation and Synthetic Application of α-Siloxy Amines
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A new and versatile synthetic intermediate, α-siloxy amine was prepared in situ by the base-promoted rearrangement of a siloxyammonium salt obtained by treatment of a tertiary amine N-oxide with trialkylsilyl trifluoromethanesulfonate.The best combination of the base and silylating reagent was found to be methyllithium and t-butyldimethylsilyl trifluoromethanesulfonate.The reactions of α-siloxy amines with acyl halides and haloformates gave the corresponding amides and carbamates in moderate to good yields, respectively.Treatment of α-siloxy amines with acetic acid resulted in a direct dealkylation to free secondary amines.Fluoride induced alkylation of α-siloxy amines using alkyl halides as electrophiles leading to tertiary amines was also examined and demonstrated to be a new transalkylation method of amines.
- Tokitoh, Norihiro,Okazaki, Renji
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p. 3291 - 3298
(2007/10/02)
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- FLUORIDE INDUCED ALKYLATION OF α-SILOXYAMINES. A NEW METHOD FOR TRANSALKYLATION OF TERTIARY AMINES VIA THEIR N-OXIDES
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α-Siloxyamines obtained from tertiary amines via their N-oxides react with alkyl halides to give the corresponding α-siloxyammonium salts, which can be converted into new tertiary amines by fluoride induced desilylation reaction.
- Tokitoh, Norihiro,Okazaki, Renji
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p. 1937 - 1938
(2007/10/02)
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- NOVEL APPLICATIONS OF α-AMINOSUBSTITUTED DIPHENYLPHOSPHINE OXIDES. THE CONVERSION OF ALDEHYDES INTO α-AMINOMETHYLKETONES.
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Aromatic and aliphatic aldehydes (R3CHO) can be converted into α-aminomethylketones (R3COCH2NR1R2) via reaction with (α-aminomethyl)diphenylphosphine oxides.
- Broekhof, Nico L.J.M.,Gen, Arne van der
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p. 2799 - 2802
(2007/10/02)
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