- Insights into Substrate Self-Assisted Activation of Allylic Alcohols Guiding to Mild Allylic Substitution of Tautomerizable Heteroarenes
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A substrate self-assisted activation of allylic alcohols by tautomerizable heteroarenes via hydrogen bonding was disclosed by various NMR techniques, including variable-temperature 1H NMR, Job plot, and 1H NMR titration. Guided by th
- Cao, Xinhua,Huang, Lijun,Liu, Aoqi,Ma, Bing,Ma, Xiantao,Yu, Jing,Zheng, Lingyun,Zhou, Qiuju
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- Properties of 2-Iodomethyl-2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium Triiodide
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2-Iodomethyl-2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium triiodide was synthesized by the reaction of 1-allylpyridin-2(1H)-one with hydrogen iodide in the presence of hydrogen peroxide or with iodine in acetone. The title compound reacted with palladium(II) iodide in DMSO to give crystalline bis(2-iodomethyl-2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium) di-μ2-iodido-tetraiodidodipalladate(II) whose structure was proved by X-ray analysis. The reaction of 2-iodomethyl-2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium triiodide with sodium iodide in acetone afforded 2-iodomethyl-2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium iodide which decomposed into initial 1-allylpyridin-2(1H)-one and iodine on heating in methanol.
- Kim,Kalita,Sharutin,Senchurin,Belov
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- Environmentally benign nucleophilic substitution reaction of arylalkyl halides in water using CTAB as the inverse phase transfer catalyst
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An environmentally benign, practically scalable and highly selective C-arylalkylation of active methylene compounds is developed using CTAB as the inverse phase transfer catalyst in water. The methodology developed is elaborated into the one-pot synthesis of quinoline derivatives and also applicable to the regioselective N-aralkyl of 2-pyridones.
- Godha, Atul K.,Thiruvengadam, Jayaraman,Abhilash, Viswanadhan,Balgi, Prajwal,Narayanareddy,Vignesh, Kumaresan,Gadakh, Amol V.,Sathiyanarayanan,Ganesh, Sambasivam
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supporting information
p. 16041 - 16045
(2019/10/28)
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- Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
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A specific N-alkylation of 2-hydroxypyridines is achieved by reacting with organohalides under catalyst- and base-free conditions. The observed HX-facilitated conversion of pyridyl ether intermediates to 2-pyridone products may account for the success and
- Feng, Bin,Li, Yang,Li, Huan,Zhang, Xu,Xie, Huamei,Cao, Hongen,Yu, Lei,Xu, Qing
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p. 6769 - 6775
(2018/05/29)
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- Iron-catalyzed regioselective direct arylation at the C-3 position of N-alkyl-2-pyridone
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A number of pharmaceutical compounds possess an arylated 2-pyridone moiety. The existing reports using expensive starting materials and/or superstoichiometric metal salts have prompted us to explore a possible user-friendly method for their synthesis. In this report, we demonstrate an easy-to-handle reaction condition with an iron catalyst for the exclusive generation of C-3-arylated pyridone via C-H functionalization.
- Modak, Atanu,Rana, Sujoy,Maiti, Debabrata
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p. 296 - 303
(2016/09/09)
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- Scope and limitations of the synthesis of functionalized quinolizidinones and related compounds by a simple precursor approach via addition of lithium allylmagnesates to 2-pyridones and RCM as key steps
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The scope and limitations of the simple synthesis of functionalized quinolizidin-4-ones by chemoselective N-alkenylation of NH pyridin-2(1H)-ones (2-pyridones), regioselective addition of lithium allyl(di-n-butyl)magnesates(1-) to N-alkenylpyridin-2(1H)-ones, followed by ring closing metathesis (RCM) is described. A number of functionalizations introduced into quinolizidin-4-one rings demonstrated the high prospect of the strategy proposed in scaffold synthesis. Their extension to the syntheses of pyrido[1,2-a]azepin-4-one and pyrido[1,2-a]azocin-4-one derivatives as well as to spiro-fused compounds is also presented.
- Sos?nicki, Jacek G.,Struk, ?ukasz,Idzik, Tomasz,Maciejewska, Gabriela
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p. 8624 - 8635
(2014/12/11)
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- Design, synthesis, antiviral, and cytostatic evaluation of novel isoxazolidine analogs of homonucleotides
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Moderate diastereoselectivities (d.e. 2-62%) of isoxazolidine homonucleotides were observed for cycloadditions between N-methyl-C- (diethoxyphosphoryl)nitrone and N-allyl nucleobases, with trans-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on 2D NOE experiments performed for uracil-containing cycloadducts. The cis- and trans-isoxazolidine phosphonates obtained herein were evaluated in vitro for activity against a broad range of DNA and RNA viruses. None of the compounds were endowed with antiviral activity at subtoxic concentrations, but some of them were found to inhibit the proliferation of L1210 cells with IC50 values in the range of 33-100 μM.
- Lysakowska, Magdalena,Balzarini, Jan,Piotrowska, Dorota G.
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p. 341 - 353
(2014/05/20)
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- On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents
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The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of α,β-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids.
- Heller, Stephen T.,Sarpong, Richmond
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scheme or table
p. 8851 - 8859
(2011/12/02)
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- Alkylation of the 2-hydroxypyridine anion in ionic liquid media
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The alkylation reaction of the ambident 2-hydroxypyridine anion was examined in ionic liquid media. Ionic liquids increase the alkylation reaction rate in comparison with molecular liquids, as well as the level of impact on the reaction rates of the count
- Vavilina,Zicmanis,Mekss,Klavins
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p. 549 - 558
(2013/07/27)
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- Palladium-catalyzed rearrangement/arylation of 2-allyloxypyridine leading to the synthesis of n-substituted 2-pyridones
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(Matrix presented) The Pd-catalyzed one-pot rearrangement/arylation of 2-allyloxypyridine is described. The catalyst/base combination of Pd[P(t-Bu)3]2/Ag2CO3 was found to be optimal for this one-pot rearrangemen
- Itami, Kenichiro,Yamazaki, Daisuke,Yoshida, Jun-Ichi
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p. 2161 - 2164
(2007/10/03)
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- Regioselective synthesis of N-alkyl pyridones
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The regioselective synthesis of N-alkyl pyridones can be facilitated by alkylation of 2-methoxypyridines with activated halides. The syntheses are facile and high yielding with no traces of 2-alkoxypyridines.
- Bowman, W. Russell,Bridge, Colin F.
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p. 4051 - 4059
(2007/10/03)
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- Palladium-catalyzed allylation of pyrimidine-2,4-diones (uracils) and of 6-membered heterocyclic ambident sulfur nucleophiles
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Pd(O)-Catalyzed allylation of six-membered ambident heterocycles bearing NH-CO, NH-CS and CH2-CO moieties obey the regioselectivity rules: C>O; N>O; S>N; NH-CO>NH-CS. Uracil and 5-methyluracil (thymine) do not show regioselectivity (N-1 = N-3) whereas 6-methyluracil is regioselectively allylated at N-3 (N-3>N-1).
- Moreno-Manas,Pleixats,Villarroya
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p. 1457 - 1464
(2007/10/02)
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