78523-90-7Relevant academic research and scientific papers
Diorganyl Diselenides and Iron(III) Chloride Drive the Regio- And Stereoselectivity in the Selenation of Ynamides
Goulart, Tales A. C.,Back, Davi Fernando,Moura E. Silva, Sidnei,Zeni, Gilson
, p. 980 - 994 (2021)
We report here our results on the application of ynamides as substrates in the reactions with diorganyl dichalcogenides and iron(III) chloride to give selectively three different types of compounds: E-α-chloro-β-(organoselenyl)enamides, 4-(organochalcogenyl)oxazolones, and vinyl tosylates. The results reveal that the selectivity in the formation of products was obtained by controlling the functional groups directly bonded to the nitrogen atom of the ynamides. Thus, α-chloro-β-(organoselenyl) enamide derivatives were exclusively obtained when the TsN- and MsN-ynamides were treated with a mixture of diorganyl diselenides (1.0 equiv) and FeCl3 (3.0 equiv) in dichloroethane (DCE, 3 mL), at room temperature. The 4-(organochalcogenyl)oxazolones were selectively obtained with ynamides having an ester group, directly bonded to the nitrogen atom, upon treatment with a solution of FeCl3 (1.5 equiv) and diorganyl dichalcogenides (1.0 equiv) in dichloromethane (3 mL) at room temperature. Finally, vinyl tosylates were obtained from ynamides having an ester group, directly bonded to the nitrogen atom, by reaction with p-toluenesulfonic acid. We also studied the application of the prepared compounds as substrates for Suzuki and Sonogashira cross-coupling reactions.
Efficient Conversion of Oxazoline-2-thione to Its 2-Oxo Derivative
Roy, Jalpana,Mehrotra, K. N.
, p. 353 - 354 (2007/10/02)
4,5-Diphenyl-3-p-tolyl-4-oxazoline-2-thione (1) has been converted 2-oxo analogue (2) using (i) methyl iodide and methanol, (ii) sodium nitrite and dil.HCl and (iii) mercuric oxide, acetic anhydride and water.
Cyclization of Dianions from 2-Imino-1,2-diphenylethanone to Oxazolines, Oxazocines, and Oxazonines
Mehrotra, Kailash Nath,Singh, Indra Sen,Roy, Jalpana
, p. 2399 - 2402 (2007/10/02)
The reaction of 2-imino-1,2-diphenylethanone with sodium in ether and subsequent addition of carbon disulfide or ethyl chloroformate resulted in the formation of 3,4,5-trisubstituted 4-oxazoline-2-thiones and 2-ones, respectively. 1,4-Oxazonines and 1,4-o
Substitution and Addition Reactions at Spiro-Oxiranes
Siegel, Hannes,Wittmann, Helga
, p. 1005 - 1018 (2007/10/02)
Nucleophilic substitution at the spiro carbon atom as well as the CH2-group takes place with spiro-oxiranes 1, 6 and 7, whose spiro carbon atom bear electron withdrawing substituents.In some cases by elimination of formaldehyde a transformation to the cor
Keteimines as Intermediates to Heterocycles. Part 3. Rearrangement of 3-Iminoisoxazolines to 2-Imino-oxazolines
Sarlo, Francesco De,Guarna, Antonio,Mascagni, Paolo,Carrie, Robert,Guenot, Pierre
, p. 1367 - 1370 (2007/10/02)
N-Substituted hydroxylamines (2) add to 2-benzoyl-N,2-diphenylvinylideneamine (1) and the adducts are easily dehydrated to give the 3-iminoisoxazolines (4).Compounds (4) with 2-aryl substituents rearrange spontaneously to give the 2-imino-oxazolines (5) or (6), but the 2-methyl derivative is more stable and only rearranges on heating. 2-Imino-3-acylaziridines (8) or (9) are assumed to be the intermediates; the expected 2-imino-oxazoline (5b) was isolated among the products during an attempted synthesis of 1,3-diphenyl-2-phenylimino-3-benzoylaziridine (8b) from benzoylphenylcarbene and diphenylcarbodi-imide.
