88406-98-8Relevant academic research and scientific papers
Successively recycle waste as catalyst: A one-pot wittig/1,4-reduction/paal-knorr sequence for modular synthesis of substituted furans
Chen, Long,Du, Yi,Zeng, Xing-Ping,Shi, Tao-Da,Zhou, Feng,Zhou, Jian
, p. 1557 - 1560 (2015/03/30)
A one-pot tandem Wittig/conjugate reduction/Paal-Knorr reaction is reported for the synthesis of di- or trisubstituted furans. This novel sequence first demonstrates the possibility of successively recycling waste from upstream steps to catalyze downstream reactions.
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.
Room-temperature electrophilic 5-endo-dig chlorocyclization of alk-3-yn-1-ones with the use of pool sanitizer: Synthesis of 3-chlorofurans and 5-chlorofuropyrimidine nucleosides
Sniady, Adam,Morreale, Marco S.,Wheeler, Kraig A.,Dembinski, Roman
scheme or table, p. 3449 - 3452 (2009/04/10)
The 5-endo-dig chlorocyclization of 1,4-disubstituted alk-3-yn-1-ones (propargylic ketones) with the use of trichloro-striazinetrione (trichloroisocyanuric acid, TCCA; 0.4 equiv.) in toluene, at room temperature, in the absence of base, provides 2,5-disubstituted 3-chlorofurans in high yields (79-96%). The reaction can be accomplished by using commercially available swimming pool sanitizer. Selected 3-chlorofuran was validated as a substrate for Suzuki-Miyaura coupling. In a similar manner, chlorocyclization of 5-alkynyl-2′-deoxyuridines produces 5-chlorofuropyrimidine nucleosides (76-83%), which are analogues of potent anitviral agents. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
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
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.
