29113-63-1Relevant academic research and scientific papers
Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
Pace, Domenic P.,Robidas, Rapha?l,Tran, Uyen P. N.,Legault, Claude Y.,Nguyen, Thanh Vinh
, p. 8154 - 8171 (2021/06/28)
Substituted pyrans and furans are core structures found in a wide variety of natural products and biologically active compounds. Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine, a simple and inexpensive catalyst. The method described is performed under solvent-free conditions at an ambient temperature and atmosphere, thus offering a facile and practical alternative to currently available reaction protocols. A combination of experimental studies and density functional theory calculations revealed interesting mechanistic insights into this seemingly simple reaction.
Preparation of polysubstituted dihydrofurans through a PhI(OAc)2-promoted haloenolcyclization of olefinic dicarbonyl compounds
Liu, Ji,Liu, Qing-Yun,Fang, Xing-Xiao,Liu, Gong-Qing,Ling, Yong
supporting information, p. 7454 - 7460 (2018/10/24)
A metal-free cyclization of olefinic dicarbonyl compounds for the synthesis of various 5-halomethyl-4,5-dihydrofurans is presented. Using (diacetoxyiodo)benzene as the reaction promoter and halotrimethylsilane as the halogen source, the intramolecular hal
Method for preparing poly-substituted furan compound by condensing tricarbonyl compound under effect of titanium tetrachloride
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Paragraph 0064-0066, (2017/11/04)
The invention provides a method for preparing a poly-substituted furan compound by condensing a tricarbonyl compound under an effect of titanium tetrachloride. The method comprises the following steps: by taking methylene dichloride or methylbenzene as a solvent, causing the tricarbonyl compound react with titanium tetrachloride while stirring under inert gas shielding, ending the reaction and then separating, thereby acquiring the poly-substituted furan compound. The compounding method provided by the invention has the characteristics of easily acquired raw materials, low cost, mild reaction condition, simple and easily controlled operation, less side reaction, simple post-processing, higher product yield, capability of greatly saving production cost, higher economic benefit and suitability for industrial mass production.
Understanding the Scope of Feist–Bénary Furan Synthesis: Chemoselectivity and Diastereoselectivity of the Reaction Between α-Halo Ketones and β-Dicarbonyl Compounds
Peng, Yi,Luo, Juan,Feng, Qiang,Tang, Qiang
, p. 5169 - 5179 (2016/10/26)
Feist–Bénary furan synthesis, the reaction between α-halocarbonyl and β-dicarbonyl compounds, has been known as an efficient method for generating many different types of furans containing a carbonyl group at C-3. However, it has also been reported that, under similar reaction conditions, intermediate tricarbonyl species could be further converted to alternative furan isomers through the application of a Paal–Knorr synthesis. In this manuscript, we investigate the chemoselectivity and diastereoselectivity of furan synthesis from α-halo ketones and β-dicarbonyl compounds, by carrying out the separation and characterization of the intermediates involved in the reaction. Additionally, a one-pot Feist–Bénary furan synthesis from α-halo ketones and β-dicarbonyl compounds without any base or solvent has also been developed.
Design, synthesis and antifungal activity of novel furancarboxamide derivatives
Wen, Fang,Jin, Hong,Tao, Ke,Hou, Taiping
, p. 244 - 251 (2016/05/24)
Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.
Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)
Zhao, Dongmei,Sun, Bin,Ren, Jinhong,Li, Fengrong,Song, Shuai,Lv, Xuejiao,Hao, Chenzhou,Cheng, Maosheng
, p. 1356 - 1365 (2015/03/04)
All-trans-retinoic acid (ATRA), the biologically active metabolite of vitamin A, is used medicinally for the treatment of hyperproliferative diseases and cancers. However, it is easily metabolized. In this study, the leading compound S8 was found based on virtual screening. To improve the activity of the leading compound S8, a series of novel S8 derivatives were designed, synthesized and evaluated for their in vitro biological activities. All of the prepared compounds showed that substituting the 5-chloro-3-methyl-1-phenyl-1H-pyrazole group for the 2-tertbutyl-5-methylfuran scaffold led to a clear increase in the biological activity. The most promising compound 32, with a CYP26A1 IC50 value of 1.36 μM (compared to liarozole (IC50 = 2.45 μM) and S8 (IC50 = 3.21 μM)) displayed strong inhibitory and differentiation activity against HL60 cells. In addition, the study focused on the effect of β-phenylalanine, which forms the coordination bond with the heme of CYP26A1. These studies suggest that the compound 32 can be used as an appropriate candidate for future development.
Selective synthesis of 2,5-disubstituted furan-3-carboxylates and the isomeric 2,4-disubstituted furan-3-carboxylates
Chen, Panpan,Meng, Yinggao,Yang, Qinghua,Wu, Jie,Xiao, Yuanyuan,Gorja, Dhilli Rao,Song, Chuanjun,Chang, Junbiao
, p. 79906 - 79914 (2015/10/06)
An unprecedented Ag2CO3 and DBU mediated cyclization of 3-substituted 2-(2-bromoallyl)-3-oxo-1-carboxylates leading to the formation of 2,5-disubstituted furan-3-carboxylates has been reported. In the absence of a silver salt, the is
Indium-catalyzed synthesis of furans and pyrroles via cyclization of α-propargyl-β-keto esters
Tsuji, Hayato,Yamagata, Ken-Ichi,Ueda, Yasuyuki,Nakamura, Eiichi
, p. 1015 - 1017 (2011/06/17)
In(OTf)3 or In(NTf2)3 effectively catalyze the cyclo-isomerization reaction of -propargyl - keto esters and their imine analogues to afford trisubstituted furans and pyrroles, respectively. Both terminal and internal alkyn
Ionic liquid as catalyst and reaction medium: A Simple and Efficient Procedure for Paal-Knorr furan synthesis
Wang, Gangqiang,Guan, Zhi,Tang, Rongchang,He, Yanhong
experimental part, p. 370 - 377 (2010/04/04)
The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, efficiently catalyzes Paal-Knorr furan synthesis without any organic solvent. A wide range of aliphatic and aromatic 1,4-diketones easily undergo condensations to form furan derivatives, providing a general and convenient procedure. The Paal-Knorr reaction of ester-substituted 1,4-diketones is first reported. The ionic liquid can be recovered and reused for subsequent runs without any appreciable loss of efficiency.
Synthesis of pyrroles by gold(I)-catalyzed amino-claisen rearrangement of N-propargyl enaminone derivatives
Saito, Akio,Konishi, Tomoyo,Hanzawa, Yuji
supporting information; experimental part, p. 372 - 374 (2010/03/25)
(Figure presented) The cationic N-heterocyclic carbene-gold(I) complex catalyzes the formation of tri- and tetrasubstituted pyrroles via the amino-Claisen rearrangement of N-propargyl β-enaminone derivatives and the cyclization of α-allenyl β-enaminone in
