68630-12-6Relevant academic research and scientific papers
Base-catalysed [3 + 2] cycloaddition of propargylamines and aldehydes to substituted furans
Shen, Jinhai,Zhao, Jing,Hu, Bing,Chen, Yangxin,Wu, Longqiao,You, Qihua,Zhao, Li
supporting information, p. 600 - 603 (2018/02/14)
A base-catalysed [3 + 2] cycloaddition reaction of propargylamines and aldehydes for the regiospecific synthesis of substituted furans under metal-free conditions is developed. Propargylamines are used as allenyl anion equivalents and applied in [3 + 2] cycloaddition reactions with aldehydes. Various substituted furans are provided up to 91% yield for 28 examples.
X-ray Absorption and Electron Paramagnetic Resonance Guided Discovery of the Cu-Catalyzed Synthesis of Multiaryl-Substituted Furans from Aryl Styrene and Ketones Using DMSO as the Oxidant
Wu, Yong,Huang, Zhiyuan,Luo, Yi,Liu, Dong,Deng, Yi,Yi, Hong,Lee, Jyh-Fu,Pao, Chih-Wen,Chen, Jeng-Lung,Lei, Aiwen
supporting information, p. 2330 - 2333 (2017/05/12)
The first example of DMSO serving not only as a solvent but also as an oxidant to promote the oxidation of Cu(I) to Cu(II) has been demonstrated. X-ray absorption and electron paramagnetic resonance evidence revealed a single-electron redox process where DMSO could oxidize Cu(I) to Cu(II). The novel discovery guided the rational design of copper-catalyzed oxidative cyclization of aryl ketones with styrenes to furans, providing a new method for the synthesis of multiaryl-substituted furans from cheap and readily available starting materials.
Radical based strategy toward the synthesis of 2,3-dihydrofurans from aryl ketones and aromatic olefins
Naveen, Togati,Kancherla, Rajesh,Maiti, Debabrata
supporting information, p. 5446 - 5449 (2015/01/09)
A copper-mediated annulation of aryl ketones with a wide range of aromatic olefins has been developed. This strategy allowed convenient access to 2,3-dihydrofuran derivatives. The versatility of the protocol is shown by synthesizing α-methyl dihydrofurans, which serve as an intermediate for the synthesis of vitamin B1. In addition, the applicability of the protocol in conjugated systems is demonstrated. A radical pathway was presumed and supported for annulation of aryl ketones with olefins. (Chemical Equation Presented).
Bronsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans
Mothe, Srinivasa Reddy,Lauw, Sherman Jun Liang,Kothandaraman, Prasath,Chan, Philip Wai Hong
, p. 6937 - 6947 (2012/10/07)
A Bronsted acid-catalyzed method to prepare tri- and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH?H 2O-mediated tandem alkylation/cycloisomerization of the propargylic 1,4-diol with the β-dicarbonyl compound was found to selectively occur to provide the tetrasubstituted furan product. On the other hand, increasing the reaction temperature to 80 °C was discovered to result in preferential p-TsOH?H2O-catalyzed dehydrative rearrangement of the unsaturated alcohol and formation of the 2,3,5-trisubstituted furan adduct.
Influence of Wavelength on the Photochemistry of Triarylbenzofurodioxin Derivatives
Horspool, William M.,Khalaf, Abedawn I.
, p. 1147 - 1152 (2007/10/02)
The u.v. irradiation of a number of triarylfurobenzodioxins has been carried out at both λ >280 nm and at 254 nm.The outcome of the reaction is to some extent dependent both on the substitution pattern on the bridgehead (9a) aryl group and on the waveleng
Facile Synthesis of Furans From 2-Ene-1,4-diones by Diphosphorus Tetraiodide
Demirdji, S. H.,Haddadin, M. J.,Issidorides, C. H.
, p. 495 - 496 (2007/10/02)
Diphosphorus tetraiodide effects reductive ring-closure of a variety of 2-ene-1,4-diones into furans within a few minutes at room temperature.
SUBSTITUENT AND WAVELENGHT EFFECT IN THE PHOTOCHEMISTRY OF 5,6,7,8-TETRACHLORO-3a,9a-DIHYDRO-2,3,9a-TRIARYLFURO(2,3-b)(1,4)BENZODIOXIN DERIVATIVES
Horspool, William M.,Khalaf, Abedawn I.
, p. 3745 - 3748 (2007/10/02)
A study of the photoreactions of some triarylfurobenzodioxin derivatives has shown that the outcome is dependent on the type and position of the substitution on the 9a-aryl group.A wavelenght dependence is also reported.
