117203-31-3Relevant academic research and scientific papers
Dienediones as Building Blocks of an Unfused Polyaromatic Furan Ring System with Tunable Regioselectivity
Ong, Chi Wi,Chen, Chong-Ming,Juang, Shyh Shiaan
, p. 3135 - 3138 (1995)
The 1,6-dioxo (E,E)-diene has two available sites for isomerization to the (Z) configuration and can undergo an intramolecular acid-catalyzed cyclization to furanonium intermediates A and B, giving two distinct regioisomeric cyclized products.With unsubstituted aryl derivatives, unfused polyaromatic furans were obtained in good yield with HCl-AcOH.Aryl groups having electron-withdrawing substituents were found to give the opposite regioselectivity.In contrast, the reaction in p-TsOH-CH2Cl2 always resulted in a mixture of regioisomeric products, irrespective of the aryl substituents.Thus, the regioselectivity in the intramolecular cyclization of 1,6-dioxo 2,4-diene can be tuned by varying the aromatic aubstituents and the acid conditions.
Synthesis of Isoxazolylvinyl Ketones from Substituted Furans
Abaev, Vladimir T.,Hampel, Frank,Serdyuk, Olga V.
, (2020)
[Figure not available: see fulltext.] A new method for the preparation of isoxazolylvinyl ketones related to potential cytotoxic agents has been developed. In the first step, the reaction of furfuryl ketones with hydroxylamine hydrochloride affords the corresponding oximes. Further, the oxidative ring opening – ring closure reaction of oximes leads to isoxazoles with an α, β-unsaturated carbonyl motif. The developed procedure is metal-free and does not require expensive starting materials.
Synthesis of pyrazolylvinyl ketones from furan derivatives
Sawengngen, Nattawut,Chalikidi, Petrakis N.,Araby, Sara,Hampel, Frank,Gmeiner, Peter,Serdyuk, Olga V.
, p. 4850 - 4855 (2019/05/24)
A new protocol for the synthesis of pyrazol-5-ylvinyl ketones, e.g. pyrazole-chalcones, employing furfuryl ketones as a triketone equivalent, has been developed. The reaction occurs under mild conditions and does not require the use of expensive materials
Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2- substituted furans: Application to the biomimetic synthesis of merrekentrone C
Gryparis, Charis,Lykakis, Ioannis N.,Efe, Christina,Zaravinos, Ioannis-Panayotis,Vidali, Theonymphi,Kladou, Eugenia,Stratakis, Manolis
, p. 5655 - 5658 (2011/09/16)
Photooxygenation of (β-keto)-2-substituted furans leads, in a one pot operation, to functionalized 3(2H)-furanones with good to excellent yields. This methodology was applied as a key-step to the concise and biomimetic synthesis of the sesquiterpene merre
Gold catalysis: benzanellation versus alkylidenecyclopentenone synthesis
Hashmi, A. Stephen K.,W?lfle, Michael
experimental part, p. 9021 - 9029 (2009/12/08)
A series of different furan-yn-ols were prepared by a three-step sequence. Their reaction with Gagosz's catalyst Ph3PAuNTf2 depends strongly on the substitution pattern of the substrate and the quality of the leaving group. Benzofurans, alkylidenecyclopentenones or Meyer-Schuster type products can be obtained. Improving the leaving group quality leads to the preferred formation of benzofurans.
Elimination Reactions of Terminal β-Oxy Selenoxides. Synthesis of Aryl and Vinyl Enol Ethers and of Furans, Oxazoles, and Thiazoles
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Marini, Francesca
, p. 1349 - 1354 (2007/10/02)
Elimination reactions of terminal selenoxides holding an alkoxy group in the β-position, RCH(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures.We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR).These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers.Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans.The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.
A NEW APPROACH TO POLYFUNCTIONAL 3(2H)-FURANONES
Antonioletti, Roberto,Bonadies, Francesco,Prencipe, Teresa,Scettri, Arrigo
, p. 629 - 632 (2007/10/02)
A selective oxidative opening of the heterocyclic nucleus of 2-(acylmethyl)-5-methylfurans or 2-(5-methyl-2-furyl)-1,3-dicarbonyl compounds by m-chloroperbenzoic acid allows the one-pot synthesis of 3(2H)-furanone derivatives.The same methodology, extende
