88089-34-3Relevant academic research and scientific papers
Copper-catalyzed direct synthesis of furans and thiophenes via decarboxylative coupling of alkynyl carboxylic acids with H2O or Na2S
Irudayanathan, Francis Mariaraj,Edwin Raja, Gabriel Charles,Lee, Sunwoo
, p. 4418 - 4425 (2015/06/08)
2,5-Diaryl-substituted furans were synthesized from the copper-catalyzed decarboxylative coupling of aryl-substituted aryl propiolic acids in the presence of H2O. The homocoupling of alkynyl carboxylic acids provided 1,4-diaryldiynes, which then reacted with H2O to give the desired furans through cyclization. Addition of the copper catalyst was critical, and the addition of a ligand increased the yield of products in both the homocoupling and cyclization reactions. In addition, thiophenes could be obtained when the reaction was conducted in the presence of Na2S.
Copper(II)-Promoted, One-Pot Conversion of 1-Alkynes with Anhydrides or Primary Amines to the Respective 2,5-Disubstituted Furans or Pyrroles under Microwave Irradiation Conditions
Lee, Hyejeong,Yi, Yeonhui,Jun, Chul-Ho
, p. 3485 - 3490 (2016/01/25)
Furans and pyrroles are prepared from 1-alkynes by using a Cu(II)-promoted, one-pot, microwave irradiation method. Glaser coupling of 1-alkynes and cyclization of the resulting 1,3-diyne in the presence of an anhydride or a primary amine results in the formation of the respective 2,5-diaryl- or 2,5-dialkyl-substituted furans and pyrroles.
Gold-catalyzed formation of C-O and C-C bonds: An efficient domino reaction synthesis of functionalized furans
Guo, Pengfeng
, p. 58 - 60 (2015/05/13)
An efficient gold-catalyzed domino reaction for the synthesis of furan derivatives from haloalkynes has been described. This transformation has provided a new route for the formation of C-O and C-C bonds that prepare functionalized furans.
A general approach to arylated furans, pyrroles, and thiophenes
Zheng, Qingwei,Hua, Ruimao,Jiang, Jianhua,Zhang, Lei
, p. 8252 - 8256 (2015/03/05)
A general and practical synthetic method for aryl-substituted five-membered heterocycles has been developed. In the presence of KOH (30%), 1,4-diaryl-1,3-butadiynes undergo the cyclocondensation reaction with water, primary amines, and Na2S·9H2O in DMSO at 80 °C to afford 2,5-diarylfurans, 1,2,5-trisubstituted pyrroles, and 2,5-diarylthiophenes in good to high yields. Further studies have disclosed that aryl-substituted five-membered heterocycles can be also synthesized by a one-pot, two-step strategy from the terminal alkynes in DMSO firstly catalyzed by CuCl, and then via addition of KOH to promote the cyclocondensation of 1,3-butadiynes generated in situ.
Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira-Glaser cyclization sequence
Klukas, Fabian,Grunwald, Alexander,Menschel, Franziska,Mueller, Thomas J. J.
, p. 672 - 679 (2014/04/17)
2,5-Di(hetero)arylfurans are readily accessible in a pseudo five-component reaction via a Sonogashira-Glaser coupling sequence followed by a superbase-mediated (KOH/DMSO) cyclization in a consecutive one-pot fashion. Besides the straightforward synthesis of natural products and biologically active molecules all representatives are particularly interesting due to their bright blue luminescence with remarkably high quantum yields. The electronic structure of the title compounds is additionally studied with DFT computations.
Synthesis and antiproliferative activity of RITA and its analogs
Jiang, Jianhua,Ding, Chao,Li, Lulu,Gao, Chunmei,Jiang, Yuyang,Tan, Chunyan,Hua, Ruimao
, p. 6635 - 6638 (2015/01/16)
The synthesis of RITA and a variety of five-membered heterocyclic triads by the cyclocondensation of 1,4-bis(5-substituted-2-thienyl or 2-furyl)-1,3-butadiynes with water or Na2S·9H2O in the presence of KOH in DMSO is described. The study on the antiproliferative activities against K562, MCF-7, A549, and HCT116 tumor cells has revealed that some of the heterocyclic triads show higher antiproliferative activities than RITA, depending on the structures of substituents, the property of heteroatoms as well as their numbers.
Copper(I)-catalyzed synthesis of 2,5-disubstituted furans and thiophenes from haloalkynes or 1,3-diynes
Jiang, Huanfeng,Zeng, Wei,Li, Yibiao,Wu, Wanqing,Huang, Liangbing,Fu, Wei
experimental part, p. 5179 - 5183 (2012/07/03)
A regioselective synthesis of 2,5-disubstituted furans using copper(I) catalyst from haloalkynes in a one-pot procedure has been reported. This chemistry proceeds through the hydration reaction of 1,3-diynes, which can be readily prepared from the coupling reaction of haloalkynes in the presence of CuI. The procedure also can be used for the facile synthesis of 2,5-disubstituted thiophenes.
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 Furan- and Pyrrole-Containing α-Oligothiophenes via 1,4-Diketones
Chen, Liang-Huei,Wang, Chin-Yu,Luo, Thung-Mei H.
, p. 1393 - 1398 (2007/10/02)
Cyclization of the 1,4-dithienyl-1,4-diketones (3) by acid catalyst furnished the α-thienylfurans, whereas condensation with ammonium acetate provided the α-thienylpyrroles.The 2,5-bisthiophene (5) similarly gave the first syntheses of 2,5-bisthiophene (12) and 2,5-bisthiophene (13).
SYNTHESIS AND (13)C NMR CHARACTERIZATION OF SOME π-EXCESSIVE HETEROPOLYAROMATIC COMPOUNDS
Carpita, Adriano,Rossi, Renzo,Veracini, Carlo Alberto
, p. 1919 - 1930 (2007/10/02)
Several ?-excessive heteropolyaromatic compounds, which contain furan and thiophen ring and are possible antifungal agents, have been synthesized in good yields according to two general methods.The first method has been used to prepare compounds possessing thiophens linked by their 2- and 5-positions, such as the ter-aryls 2b, 2d and 2a.Two precursors of these compounds have been obtained either by the Glaser reaction, or using a novel Pd-mediated reaction.The second method, which consists of the Ni- or Pd-catalyzed heteroarylation of heteroarene halides via cross-coupling with heteroaryl Grignard reagents or zinc halides, has been used to prepare the bi-aryls 1a-e, which contain two heteroaromatic units, and the ter-aryl 2c.Compound 1e has been also prepared starting from 2-(2-thienyl)furan (1c) by selective lithiation, followed by bromination.The (13)C NMR signals of 1a-e and 2a-d have been assigned on the basis of the literature data and by relaxation measurements.Relaxation data have been also used to obtain qualitative informations on the conformational equilibria of the bi-aryls 1a, 1c and the ter-aryls 2a-d.
