56795-82-5Relevant academic research and scientific papers
O-Heterocycles from Unsaturated Carbonyls and Dimethoxycarbene
Croisetière, Jean-Philippe,Spino, Claude
, p. 5609 - 5618 (2018/05/08)
The (4+1)-annulation of dimethoxycarbene with readily accessible α,β-unsaturated carbonyls gives cyclic orthoesters, which can then be converted in just a few steps to other O-heterocycles, including methoxyfurans, furanones, and furans.
A Heteroarylamine Library: Indium-Catalyzed Nucleophilic Aromatic Substitution of Alkoxyheteroarenes with Amines
Yonekura, Kyohei,Yoshimura, Yasuhiro,Akehi, Mizuri,Tsuchimoto, Teruhisa
, p. 1159 - 1181 (2018/02/06)
Under indium Lewis acid catalysis, electron-rich five-membered heteroaryl electrophiles fused with/without a benzene ring were found to couple with amines to produce heteroarylamines with broad structural diversity. The heteroarylamine formation proceeds through the cleavage of a heteroaryl?OMe bond by the nucleophilic attack of the amine based on the nucleophilic aromatic substitution (SNAr) reaction. In contrast to the corresponding traditional SNAr amination, the present SNAr-based heteroaryl amination can be performed without relying on both heteroaryl electrophiles with electron-withdrawing groups and nucleophilicity-enhanced metal amides. High compatibility towards the functional groups such as NO2, Br, I, CF3, CN, CO2Et, pyridyl, thiazolyl, C=C, and OH groups was observed, thus showing the practicality and reliability of this method. Mechanistic studies indicated that a carbon?indium bond is likely to be formed on the heteroaryl ring during the process. (Figure presented.).
Photosensitized Oxidation of Furans. Part 13. Trapping Reactions of the Carbonyl Oxides Obtained from Some 2-Methoxy-5-phenylfurans
Graziano, M. Liliana,Iesce, M. Rosaria,Cimminiello, Guido,Scarpati, Rachele
, p. 1699 - 1704 (2007/10/02)
The dye-sensitized photo-oxygenation in methanol of the 2-methoxy-5-phenylfurans (1a-c), unsubstituted at C-4 with electron-withdrawing groups, leads to the hemiperacetals (4a-c).The reaction provides the first incontrovertible evidence for carbonyl oxide
SYNTHESIS OF 5-ARYL-2-ALKOXYFURANES FROM 1-AROYL-2,2-DICHLOROCYCLOPROPANES
Kulinkovich, O. G.,Tishchenko, I. G.,Masalov, N. V.
, p. 1319 - 1321 (2007/10/02)
The reaction of 1-aroyl-2,2-dichlorocyclopropanes with a mixture of potassium tert-butylate and potassium methylate (or ethylate) in tert-butyl alcohol gives 5-aryl-2-methoxy(or ethoxy)furanes in good yield.
ELECTROOXIDATION OF 2-ARYLFURANS
Janda, Miroslav,Srogl, Jan,Dvorakova, Hana,Dvorak, Dalimil,Stibor, Ivan
, p. 906 - 916 (2007/10/02)
Electrochemical methoxylation of 2-phenylfuran (I) and 2-(4-nitrophenyl)furan (VI) proceeded anomalously, affording 5-methoxy-2-phenylfuran (XI) and 5-methoxy-2-(4-nitrophenyl)furan (XIII), respectively. 2-Phenyl-5-methylfuran (II) and methyl-2-(2-methylphenyl)-3-furoate (VIII) behaved normally giving the respective 2,5-dimethoxy-2,5-dihydrofuran derivatives XII and XIV.The suggested ECNECB mechanism of the anomalous methoxylation was confirmed by methoxylation of compound II, in which the methyl group hinders the last CB step, and also of compound VIII in whichthe aromaticity is suppresed by forced deviation from planarity.Forced deviation from planarity was moreover studied also on 2-(4-methylphenyl)furan (III), 5-methyl-2-(2-methylphenyl)furan (IV) and 3,5-dimethyl-2-(2-methylphenyl)furan (V) as model compounds.For all the derivatives the INDO charges were calculated and correlated with the 1H- and 13C-NMR spectra.The experimental electronic spectra were correlated with the theoretical ones (INDO-S-CI).All results obtained confirm the suggested mechanism.
