- Photoinduced, Copper-Catalyzed Three-Component Annulation of gem-Dialkylthio Enynes
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Photoinduced, copper-catalyzed three-component radical annulation of gem-dialkylthio enynes, cyclobutanone oxime esters, and boronic acids was achieved, forming highly functionalized aryl thienyl sulfides with both good chemo- and diastereoselectivities. The reaction proceeds through a domino sequence involving cyanoalkyl radical-mediated intramolecular annulation of gem-dialkylthio enyne, alkenyl radical-promoted C(sp3)-S bond cleavage, and sulfur-centered radical-trapped Cu(II)-facilitated C-S cross-coupling. The protocol features simultaneous establishment of cyanoalkyl, cyclopentanone, and thiophene moieties and a thioether C-S bond in one pot with broad substrate scopes and versatile functional group tolerance under mild conditions.
- Lou, Jiang,Ma, Juan,Xu, Bao-Hua,Zhou, Yong-Gui,Yu, Zhengkun
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supporting information
p. 5202 - 5206
(2020/07/15)
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- Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction
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The reduction of cage ketoximes under Schwenk–Papa reaction conditions was studied to establish that the d,l, d- and l-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, d,l-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.
- Brunilin, R. V.,Mkrtchyan, A. S.,Nawrozkij, M. B.,Novakov, I. A.,Vernigora, A. A.,Voloboev, S. N.,Vostrikova, O. V.
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p. 1742 - 1748
(2020/01/11)
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- AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0098; 0100; 0101; 0102
(2018/03/25)
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- Action of N-bromosuccinimide-dimethyl sulphoxide on camphor and its oxime derivative
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Reaction of N-bromosuccinimide-dimethyl sulphoxide (NBS/DMSO) has been carried out on cyclic monoterpenoid taking camphor and its 2-keto oxime derivative as the starting material. The compounds obtained as a result of the reaction have been characterized and identified by spectroscopic analysis (IR, NMR) and by mass spectral data.
- Ghosh, Pranab,Chakraborty, Prasanta,Ghosh, Ashim
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p. 1591 - 1594
(2013/03/13)
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- Silicon-catalyzed conversion of nitro compounds into ketones and poly(1,3-diketones)
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The reaction of various secondary nitro compounds with 1.1 equivalents of potassium hydride in 1,4-dioxane and then with 0.10 equivalent of chlorotrimethylsilane gave the corresponding ketones in 62-90% yields. By a similar strategy, poly(1,3-diketones) were synthesized directly from nitroalkenes with sodium ethoxide, potassium hydride, and chlorotrimethylsilane in 1,4-dioxane. The use of chlorotrimethylsilane in a catalytic amount was the key to the success of this transformation; the use of an excess of chlorotrimethylsilane led to poor yields for the same reactions. Georg Thieme Verlag Stuttgart.
- Hwu, Jih Ru,Josephrajan, Thainashmuthu,Tsay, Shwu-Chen
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p. 3305 - 3308
(2008/09/17)
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- Camphor/Longicamphor and 7β-Formylnorlongifolane/7β-Acetylnorlongifolane Oximes: A Comparative Beckmann Rearrangement Study
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Camphor oxime (3)/longicamphor oxime (4) have been shown to undergo Beckmann fragmentation on exposure to tosyl chloride in pyridine generating olefinic nitriles: 3->5+6 and 4->7+8+9; in the case of 4 this reaction provides an entry into the bicyclononane system characteristic of the secolongifolene diol fungal metabolite (10). 7β-Formylnorlongifolane oxime (14)/7β-acetylnorlongifolane oxime (15) when treated with the same Beckmann catalyst under similar conditions, afford the nitrile (16)/amide (17); on hydrolysis with base 17 gives the amine 18.Reaction of longicamphor (2) with hydroxylamine-O-sulfonic acid, however, a ffords the nitrogen-insertion product, α-longicamphidone (24) besides the fragmented nitrile (7).
- Satyanarayana, N.,Shitole, H. R.,Nayak, U. R.
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p. 997 - 1001
(2007/10/02)
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- Stereochemical Assignment of Camphoroxime by PMR Spectroscopy Using Tris(dipivalomethanato)europium(III)
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Stereochemistry of camphoroxime has been deciphered with the help of PMR spectroscopy using tris(dipivalomethanato)europium (III) as a shift reagent.The hydroxyl group in the oxime has been shown to be syn to γ-methyl on the basis of its anisotropic effect as well as the pronounced paramagnetic induced shift of the γ-methyl.Three methyl (α-, β- and γ-) resonances have also been rationalised using various concentrations of the shift reagent.
- Singh, Ashok Kumar,Verma, Shiva Mohan
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