87979-60-0Relevant academic research and scientific papers
Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones
Kiyokawa, Kensuke,Takemoto, Kenta,Yahata, Shunsuke,Kojima, Takumi,Minakata, Satoshi
supporting information, p. 2907 - 2912 (2017/06/27)
The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf) 2, which is in situ prepared from PhI(OAc) 2 and Me 3 SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5 H)-ones or furan-2(3 H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.
Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes
Gronnier, Colombe,Kramer, Soren,Odabachian, Yann,Gagosz, Fabien
, p. 828 - 831 (2012/03/07)
In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.
Palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate: An approach to 4-aryl butenolides and an expeditious synthesis of rubrolide E
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Sferrazza, Alessio
experimental part, p. 1277 - 1280 (2009/10/23)
The palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate in MeOH under mild conditions gives 4-arylbutenolides usually in good to high yields through a domino vinylic substitution/cyclization process. The rea
Butenolide annelation using a manganese(III) oxidation. A synthesis of 4-arylfuran-2(5H)-ones
Demir, Ayhan S.,Camkerten, Nurettin,Gercek, Zuhal,Duygu, Nese,Reis, Omer,Arikan, Elif
, p. 2441 - 2448 (2007/10/03)
A general procedure was developed for the annelation of a butenolide to an aromatic ketone that highlighted a manganese(III) oxidation of aromatic ketones. The oxidation of aromatic ketones with manganese(III) acetate in the presence of 2-bromoacetic acid or the Mn(II) salt of this carboxylic acid provided a regioselectively convenient synthesis of 2-(2-bromoacetoxy) ketones. An Arbuzov or Wittig reaction of 2-(2-bromoacetoxy) ketones followed by cyclisation furnished 4-arylfuran-2(5H)-ones in good yield.
Facile access to 4-aryl-2(5H)-furanones by suzuki cross coupling: Efficient synthesis of rubrolides C and E
Boukouvalas, John,Lachance, Nicolas,Ouellet, Michel,Trudeau, Martin
, p. 7665 - 7668 (2007/10/03)
The Pd(0)-catalyzed cross coupling between 4-bromo-2(5H)-furanones and arylboronic acids provides the corresponding 4-aryl-2(5H)-furanones in yields of 61-85%. By using this method in conjunction with furanolate chemistry, the marine antibiotics rubrolide C and E have been synthesized in highly efficient fashion (4 steps, overall yield = 61 and 56% respectively) from β- tetronic acid.
Simple preparation of 4-aryl- and 4-alkyl-2(5H)-furanones from β-substituted crotonic esters
Kagabu,Shimizu,Ito,Moriya
, p. 830 - 832 (2007/10/02)
Treatment of β-aryl- or β-alkylcrotonic esters with selenium dioxide in acetic acid in the presence of a catalytic amount of perchloric acid gave 4-substituted 2(5H)-furanones in moderate to good yields.
INVESTIGATIONS IN THE SERIES OF SUBSTITUTED BUTAN- AND BUTENOLIDES. III. SYNTHESIS OF ARYLBUTAN- AND ARYLBUTENOLIDES AND THEIR PROPERTIES
Chellar, N. S.,Badovskaya, L. A.,Ignatenko, A. V.
, p. 1775 - 1779 (2007/10/02)
A new method was developed for the synthesis of 2-aryl- and 3-aryl-2-buten-4-olides by the arylation of 2-buten-4-olide with diazonium halides in the presence of cupric chloride as catalyst.The intermediate products of the reaction are the corresponding arylchlorobutanolides. 4-R-Methylene-3-aryl-2-buten-4-olides and 4-hydroxy-3-aryl-2-butenamides were obtained in the reaction of 3-aryl-2-buten-4-olides with aldehydes and primary aliphatic amines respectively.Some of the synthesized compounds have antimicrobial and growth-stimulant activity.
