18476-67-0Relevant academic research and scientific papers
Method for synthesizing substituted furan
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Paragraph 0010, (2017/12/09)
Provided is a method for synthesizing substituted furan. Iodohydrocarbon and terminal propargyl alcohol produce Sonogashira coupling reaction to generate an intermediate product 3-alkyne-1-alcohol, then isomeric cyclization occurs under the effect of Dess
Asymmetric hydrogenation of disubstituted furans
Wysocki, Jedrzej,Ortega, Nuria,Glorius, Frank
supporting information, p. 8751 - 8755 (2014/08/18)
An enantioselective hydrogenation of disubstituted furans has been developed by using a chiral ruthenium catalyst with N-heterocyclic carbene ligands. This reaction converts furans into valuable enantioenriched disubstituted tetrahydrofurans.
Gold-catalyzed cycloisomerization of alk-4-yn-1-ones
Belting, Volker,Krause, Norbert
supporting information; experimental part, p. 1221 - 1225 (2009/05/30)
Depending on the substitution pattern and the solvent, the gold-catalyzed cyclization of alk-4-yn-1-ones 1 affords different oxygen heterocycles under mild reaction conditions. Alkynones with one substituent at C-3 undergo a 5-exo-dig cycloisomerization t
Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation
Pridmore, Simon J.,Slatford, Paul A.,Taylor, James E.,Whittlesey, Michael K.,Williams, Jonathan M.J.
supporting information; experimental part, p. 8981 - 8986 (2009/12/27)
Alkyne-1,4-diols are readily available substrates which are isomerised to 1,4-diketones using Ru(PPh3)3(CO)H2/xantphos as a catalyst. In situ cyclisation into furans, pyrroles and pyridazines has been achieved under suitable conditions.
2,5-Disubstituted furans from 1,4-alkynediols
Pridmore, Simon J.,Slatford, Paul A.,Williams, Jonathan M.J.
, p. 5111 - 5114 (2008/02/09)
1,4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)3(CO)H2 with Xantphos at 1 mol % loading.
1,4-Carbonylative addition of arylboronic acids to methyl vinyl ketone: a new synthetic tool for rapid furan and pyrrole synthesis
Chochois, Hélène,Sauthier, Mathieu,Maerten, Eddy,Castanet, Yves,Mortreux, André
, p. 11740 - 11746 (2007/10/03)
The rhodium catalysed 1,4-carbonylative addition of arylboronic acids to methyl vinyl ketone under carbon monoxide pressure was studied. High yields of 1,4-diketones were obtained using a catalytic system formed from Rh(COD)2BF4 (COD=1,5-cyclooctadiene) and triphenylphosphine even at very low catalyst loading (0.02 mol %). A short synthetic procedure combining this carbonylation reaction with a subsequent cyclisation step affords pyrroles or furans.
Preparation of furans by palladium-catalyzed reaction of acylchromates and propargylic tosylates
Nakamura, Masaki,Yamane, Motoki,Sakurai, Hidehiro,Narasaka, Koichi
, p. 333 - 345 (2007/10/03)
Substituted furans are prepared by the palladium-catalyzed reaction of propargylic tosylates with acylchromates. The reaction is initiated by the oxidative additiion of propagylic tosylates to palladium(O) complexes to give 1,2-propadienylpalladium(II) co
Photochemical carbon skeletal rearrangement of the Baylis-Hillman products: β-C-H activation leading to furans
Matsumoto, Shoji,Mikami, Koichi
, p. 469 - 470 (2007/10/03)
Furan ring formation was found in photochemical reaction of the methyl ether of the Baylis-Hillman products. This reaction proceeds via β-C-H activation of the photo-excited carbonyl compounds.
Further reactions of furans with trithiazyl trichloride; mechanistic considerations
Rees, Charles W.,Yue, Tai-Yuen
, p. 2247 - 2252 (2007/10/03)
The reaction of 2,5-diarylfurans with trithiazyl trichloride 1 to give 5-aroyl-3-arylisothiazoles in a useful one-step synthesis of isothiazoles has been extended to both weakly and strongly polarised unsymmetrical 2,5-diarylfurans. These react in an entirely analogous manner; the more electron releasing aryl group becomes incorporated into the 5-aroyl group of the isothiazole as the exclusive (strong polarisation) or the major (weak polarisation) product. However, with 3-bromo-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-furan 7, where the more reactive furan β-position is now substituted, this regiospecificity is reversed (to give isothiazole 8). When one of the α-aryl groups in the furan is replaced by methyl the same regiospecific isothiazole formation is now accompanied by some ring and side chain chlorination (15 → 16 + 17 + 18). All of these results can be explained by mechanisms (Schemes 2 and 5) which involve initial electrophilic attack of the furan to give a β-thiazyl derivative. This highly reactive (nitrenoid) substituent then induces a novel opening of the furan ring 21 to give a highly delocalised intermediate 22 which recyclises to the isothiazole.
Rearrangements Studies on Acylketene O-Prop-2-ynyl S-Methylmonothioketals
Bhat, Laxminarayan,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 1749 - 1752 (2007/10/02)
Acylketene O-prop-2-ynyl S-methylmonothioketals 3a-e, easily obtained through displacement on β-oxosulfonium salts 2a-e by prop-2-ynol, are shown to undergo facile rearrangement under neutral (toluene-xylene) and basic conditions (K2CO3-EtCOMe) to afford
