50626-02-3Relevant academic research and scientific papers
Phosphine-Mediated Reductive Condensation of γ-Acyloxy Butynoates: A Diversity Oriented Strategy for the Construction of Substituted Furans
Jung, Cheol-Kyu,Wang, Jian-Cheng,Krische, Michael J.
, p. 4118 - 4119 (2004)
Exposure of γ-acyloxy butynoates to stoichiometric quantities of triphenylphosphine results in reductive condensation to afford substituted furans, by way of allenic ester intermediates. As γ-acyloxy butynoates are readily obtained through condensation of ethyl propiolate with aldehydes followed by acylation, this method represents a powerful and mechanistically novel protocol for the convergent three-component construction of substituted furans. Copyright
Transition-Metal-Free Approach to Polysubstituted Furans
You, Changming,Zhang, Zhenming,Tu, Yongliang,Tang, Hong,Wang, Yuanfeng,Long, Da,Zhao, Junfeng
, p. 3902 - 3910 (2020/03/23)
A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of β-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance.
Rhodium-catalyzed synthesis of 2,3 – Disubstituted N-methoxy pyrroles and furans via [3+2] cycloaddition between metal carbenoids and activated olefins
Kuruba, Bharath Kumar,Vasanthkumar, Samuel,Emmanuvel, Lourdusamy
, p. 3093 - 3098 (2017/05/08)
For the first time, we report the synthesis of 2-substituted N-alkoxy pyrrole 3-carboxylate and furan 3-carboxylate via Rh-catalyzed [3+2] cycloaddition between α-diazo oxime ether or α-diazo carbonyl compounds with vinyl equivalents in a one-pot process. We have demonstrated ethyl vinyl ether as well as vinyl acetate as vinyl equivalents and both were found to give excellent yields. We have also demonstrated the synthesis of N-alkoxy dihydropyrrole derivatives by carrying out the reaction at low temperature.
Diethylene Glycol Serving as Ethyne Equivalent: A Sustainable Approach toward 2,3-Disubstituted Furan
Yu, Jin-Tao,Shi, Bo,Peng, Haibo,Sun, Song,Chu, Haoke,Jiang, Yan,Cheng, Jiang
supporting information, p. 3643 - 3645 (2015/08/18)
In the presence of tert-butyl peroxide (TBHP), the copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol was developed leading to 2,3-disubstituted furan. Diethylene glycol serves as a cheap and environmentally friendly equivalent of ethyne, with the release of H2O and alcohol as clean wastes. The procedure involves a sequential O- and C- functionalization of β-ketoester by diethylene glycol.
The rearrangement of tert -butylperoxides for the construction of polysubstituted furans
Zheng, Xiaojian,Lu, Shenglin,Li, Zhiping
, p. 5432 - 5435 (2013/11/19)
The Bronsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstituted furans through a sequence of base-catalyzed Kornblum-DelaMare rearrangements and acid-promoted Paal-Knorr reactions.
Facile one-pot synthesis of di- and tri-substituted furans from acyl isocyanates using trimethylsilyldiazomethane
Hari, Yoshiyuki,Iguchi, Tomoe,Aoyama, Toyohiko
, p. 1359 - 1362 (2007/10/03)
The Diels-Alder reaction of 2-substituted 4-(trimethylsilyloxy)oxazoles, which were prepared in situ from trimethylsilyldiazomethane and acyl isocyanates, with dimethyl acetylenedicarboxylate or ethyl propiolate gave furan-3,4-dicarboxylic or furan-3-carboxylic esters in good yields.
Unsaturated Sulfoxides in Organic Synthesis: A New General Furan Synthesis
Chan, Wing Hong,Lee, Albert W. M.,Chan, Eddy T. T.
, p. 945 - 946 (2007/10/02)
Furans have been efficiently synthesised by a three-step reaction sequence.Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield.Treatment of the latter with 3-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.
A NEW CONVENIENT APPROACH TO 2,3-DISUBSTITUTED FURANS
Antonioletti, Roberto,Bonadies, Francesco,Scettri, Arrigo
, p. 73 - 74 (2007/10/02)
α-Alkoxyalkylation of 1,3-dicarbonyl compounds with α-bromoacetaldehyde diethyl acetal, mediated by trimethylsilyl triflate, affords the corresponding adducts, which are conveniently transformed into 3-acyl- and 3-alkoxycarbonyl-furans in refluxing toluene.
