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Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H446NO – PubChem

 

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Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including alpha-allenyl ketones and amino-substituted heterocycles.

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In the study of the effects of auxochromes on azomethine dye color, an oxazolidinone ring in the acceptor portion of the dye was useful both as a masking group for preparation of the electron-donating hydroxyethyl group, and as an electron-withdrawing auxochrome. In the case of m-aminophenol derivatives coupled with p-phenylenediamine, there was a 15 nm bathochromic shift relative to the parent azomethine of the series (PPD-MAP)3 and a 30 nm bathochromic shift relative to the azomethine formed from PPD and AHT, which contains an electron-donating group. However, unlike many electron-withdrawing groups, the oxazolidinone group does not significantly slow the rate of oxidative coupling of the MAP derivative with the primary intermediate to form the azomethine dye; it was about 70% of that for PPD with AHT, making the oxazolidinone-containing MAP a potentially effective oxidation dye intermediate. The effect on color of an oxazolidinone moiety in the acceptor portion of an azomethine formed with a 4,5-diaminopyrazole as the primary intermediate was similar in the magnitude of the bathochromic shift. Finally, including an auxochrome (phthalimide) that is electron-withdrawing in the acceptor portion of the azomethine, but which has decreased overlap with the pi-system of the chromophore due to twisting out of plane caused by steric interactions, results in a significant hypsochromic shift.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1194NO – PubChem

 

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[reaction: see text] Coupling of a variety of substituted aryl bromides with oxazolidinones has been achieved using the Buchwald protocol for the amidation of aryl halides. This procedure is exemplified by the synthesis of two medicinally important molecules, linezolid and toloxatone.

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Direct aerobic alpha,beta-dehydrogenation of gamma, delta-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low alpha-acidity of amides and acids. Instead of alpha-C-H metalation, this reaction proceeds by beta-C-H activation, which results in enhanced alpha-acidity. Conjugated dienamides and dienoic acids were synthesized in excellent yield with this reaction, which uses a simple reaction protocol. Mechanistic experiments suggest a catalyst resting state mechanism in which both alpha-C-H and beta-C-H cleavage is accelerated.

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A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted delta-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).

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Oxazolidine – Wikipedia,
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A highly enantioselective FeII-catalyzed thia-Michael addition to alpha,beta-unsaturated carbonyl derivatives was developed. The scope of the reaction was demonstrated with a selection of aromatic, heterocyclic and aliphatic thiols, and various Michael acceptors. The corresponding beta-thioethers were obtained in good to excellent yields (up to 98%) and moderate to excellent enantioselectivities (up to 96:4 er). Unusual hepta-coordination of the metal and chelation to alpha,beta-unsaturated oxazolidin-2-one derivatives allowed the construction of a coherent model rationalizing the enantioselective event. DFT calculations support the proposed model for observed stereoselectivities.

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Oxazolidine – Wikipedia,
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The addition of xanthates and vinyldisulfones across the double bond of enamides and ene-carbamates provides access to the corresponding three-component adducts in good to excellent yields with a high level of diastereocontrol in cyclic systems. This strategy illustrates a complementary reactivity for these versatile olefins and extends their scope of application.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H909NO – PubChem

 

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alpha,beta-Unsaturated imides and alpha,beta-unsaturated esters were found to undergo alcoholysis in the presence of trimethylphosphine. The reaction is initiated by nucleophilic addition of trimethylphosphine to the double bond of the alpha,beta-unsaturated carbonyl compound. Saturated imides also undergo the alcoholysis in the presence of the corresponding alpha,beta-unsaturated imide.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H959NO – PubChem

 

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The invention provides novel GlyT2 inhibiting compounds useful in modulating, treating, or preventing: anxiolytic disorders; a condition requiring treatment of injured mammalian nerve tissue; a condition amenable to treatment through administration of a neurotrophic factor; a neurological disorder; or obesity; an obesity-related disorder.

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