6620-27-5Relevant academic research and scientific papers
Novel Photochemical Reactions of 3(2H)-Furanones
Wolff, Steven,Agosta, William C.
, p. 4707 - 4711 (1985)
Irradiation (λ 280 nm) of furanones 6-9 leads to rearrangement to enol lactones 14-17, while the di-tert-butyl-substituted derivative 10 undergoes decarbonylation to form 21.Both types of reaction are readily quenched by 2,3-dimethyl-1,3-butadiene, and a common mechanism is suggested, involving rearrangement of the furanone to an acylcyclopropanone (as 18), followed by either reverse shift to furnish enol lactone or alternatively decarbonylation to yield 21.A convenient route to 3(2H)-furanones is provided by mercuric acetate oxidation of readily available allenic ketones.
Selective palladium-mediated synthesis of racemic 4,5-disubstituted 5H- furan-2-ones from 3-ynoic acids and organic halides
Rossi, Renzo,Bellina, Fabio,Biagetti, Matteo,Mannina, Luisa
, p. 7599 - 7602 (1998)
Racemic 4,5-disubstitued 5H-furan-2-ones have been selectively Synthesized by addition of 1,21.6 equiv of aryl, alkenyl or 1-alkynyl halides and catalytic mounts of Pd(OAc)2 and a soft ligand such as tri-2- furylphosphine or triphenylarsine to
Kinetic Resolution and Dynamic Kinetic Resolution of γ-Aryl-Substituted Butenolides via Copper-Catalyzed 1,4-Hydroboration
Lee, Soyeon,Ryu, Do Hyun,Yun, Jaesook
, p. 2377 - 2381 (2021/01/04)
Kinetic resolution (KR) and dynamic kinetic resolution (DKR) of γ-aryl and heteroaryl-substituted butenolides via CuH-catalyzed 1,4-hydroboration using pinacolborane is reported. With a copper-Ph-BPE catalyst, selectivity factors were extremely high (s=>400) with regard to the kinetic resolution of β-methyl-γ-phenyl butenolide; DKR was possible in the presence of an amine base (DBU), which facilitated racemization of the starting unsaturated lactones. The reaction provided easy access to highly enantioenriched γ-butyrolactones (>99% ee) containing β,γ-substituents. (Figure presented.).
Method for synthesizing five-membered ring lactone compound from carbon dioxide in air
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Paragraph 0017; 0018; 0019; 0020, (2016/11/17)
The invention discloses a method for synthesizing a five-membered ring lactone compound from carbon dioxide in air. 1 mmol of terminal alkyne and 5-10 folds of anhydrous tetrahydrofuran are added to a dry flask under protection of nitrogen gas, 1.0 equivalent weight of n-butylithium is added at the temperature of subzero 78 DEG C, air dried by anhydrous calcium chloride is pumped into a reaction liquid by a pressure pump after 1 h and is stopped from pumping in 8-10 h, 1.0 equivalent weight of an alpha-halogenate carbonyl compound and 2.0 equivalent weight of potassium carbonate are added under protection of nitrogen gas, the mixture reacts for 3-10 h at the temperature of 100 DEG C, and the reaction is tracked through TLC (thin layer chromatography). After the mixture sufficiently reacts, the mixture is cooled to the room temperature and filtered, a solvent is removed under reduced pressure, and a product is obtained through quick silica column chromatographic purification. According to the novel method for synthesizing the five-membered ring lactone compound, carbon dioxide in the air can be absorbed, the greenhouse effect is reduced, and a series of serious problems such as global climate warming and the like caused by the greenhouse effect can be reduced. Raw materials required in the experiment are easy to obtain, the yield is high, and the application prospect is wide.
Base-mediated tandem reaction consisting of an acyl shift strategy leading to 4,5-disubstiuted furan-2(5H)-ones
Lei, Yong,Wang, Zhi-Qiang,Xie, Ye-Xiang,Yu, Shang-Ci,Tang, Bo-Xiao,Li, Jin-Heng
, p. 31 - 35 (2011/03/20)
The first example of the synthesis of 4,5-disubstiuted furan-2(5H)-ones by base-mediated tandem acyl shift/cyclization/decarbonylation reactions of aroylmethyl 2-alkynoates has been developed. This new and inexpensive tandem route allows both a C-O bond a
Synthesis of 4-aryl-substituted butenolides and pentenolides by copper-catalyzed hydroarylation
Yamamoto, Yoshihiko,Kirai, Naohiro
experimental part, p. 269 - 279 (2010/05/19)
We have investigated the effect of the type of protecting group used and the tether length of 4- and 5-hydroxy-substituted 2-alkynoates on the yields and selectivity of the product of hydroarylation. The use of methyl, methoxymethyl, and tert-butyldimethy
Stereoselective preparation of highly functionalized (Z)-3-magnesiated enoates by an iodine - Magnesium exchange reaction
Sapountzis,Dohle,Knochel
, p. 2068 - 2069 (2007/10/03)
3-Iodoenoates are converted into the corresponding alkenylmagnesium species with complete retention of configuration of the double bond; both direct reaction and copper(I)-mediated reactions with various electrophiles provide polyfunctional enoates.
Novel syntheses of α,β-unsaturated esters, α,β-unsaturated γ-lactones, and 2-alkoxypyrroles via 1,2,4-triazole-stabilized allenic anions
Katritzky, Alan R.,Feng, Darning,Lang, Hengyuan
, p. 715 - 720 (2007/10/03)
The dianion 12 (?13) of 1-(1,2,4-triazol-1-yl)phenylpropargyl ethyl ether 11 (readily prepared from phenylpropargylaldehyde diethyl acetal 8 and 1,2,4-triazole) reacts with alkyl halides, aldehydes, ketones, and α,β-unsaturated ketones to give exclusively γ-substituted allenic products of type 10. These adducts underwent mild in situ hydrolysis enabling convenient syntheses of α,β-unsaturated esters 9a-c and α,β-unsaturated γ-lactones 16, 18, 20, and 22. Reactions of dianion 13 with imines generated the 1,3,4-trisubstituted 2-alkoxypyrroles 27, 30, and 31 in high yields. The alkylsubstituted analog 34 underwent similar reactions to give predominantly the γ-products 39, 40, and 42 along with a small proportion of α-analogs.
Neue Synthesen und Reaktionen ungesaettigter Heterotitanacyclen
Duerr, Stefan,Hoehlein, Udo,Schobert, Rainer
, p. 89 - 96 (2007/10/02)
Dicarbonyltitanocene reacts chemoselectively with difunctional carbonyl compounds such as 1,2-diketones and 1,4-diketo-2-enes, with α-ketothioketones, α-ketoimines and azodicarbonic esters and -amides to yield the corresponding, mostly new, heterotitanacycles that are capable of a lot of a useful follow-up reactions.These chelate complexes, containing three to four heteroatoms, allow the substitution of the entire titanocene fragment by carbon (formation of vinylenic carbonates and the thia-derivatives of these) or by further heteroatoms like boron or phosphorus(formation of boroles and phosphonic acid derivatives), thus retaining the cyclofunctionality.Alternatively, some of the new chelate complexes can be readily C-C-chain-lengthened via a deprotonating/alkylating sequence, leaving the metallacycle unaffected.
Cumulated Ylides, XIV - Phosphacumulene Ylides - Building Blocks for the Synthesis of Heterocyclic Compounds
Bestmann, Hans Juergen,Schmid, Guenter,Sandmeier, Dieter,Schade, Gerold,Oechsner, Helmut
, p. 1709 - 1719 (2007/10/02)
Phosphacumulene ylides 1 and acidic compounds 4 combine to give phosphoranes 5, which cyclize by an intramolecular reaction (mostly Wittig reaction) with formation of heterocycles 7.
