51061-85-9

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2473, 1983 DOI: 10.1016/S0040-4039(00)81958-9

InChI:InChI=1/C6H4O/c1-2-6-3-4-7-5-6/h1,3-5H

Upstream product

• 86842-14-0 3-Trimethylsilanyl-4-trimethylsilanylethynyl-furan 
• 498-60-2 furan-3-carboxaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 145397-30-4 C₈H₂₁N₄PSi 

Downstream Products

• 97521-91-0 (4S,4aR,8S,8aS)-8-Benzyloxymethyl-4-furan-3-ylethynyl-4-hydroxy-3,4a-dimethyl-4a,5,8,8a-tetrahydro-4H-naphthalen-1-one 
• 6617-37-4 5Z-5-[E-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ylidene]-3-methyl-2(5H)-furanone 

Relevant academic research and scientific papers

Z-ore E-configurated γ-alkylidenebutenolides from a 2- (trimethylsiloxy)furan and iodomethacrolein - Stereoselective synthesis of Z- and E-freelingyne

The γ-(α-hydroxylalkyl)butenolides lk-5 and ul-5 were prepared by Mukaiyama aldol additions between iodoaldehyde 10 and the trimethylsiloxy-substituted furan 6 in the presence of BF3·OEt2 and ZnBr2, respectively. Couplings of these butenolides with 3- ethynylfuran followed by anti-eliminations of water mediated by DEAD/PPh3 led to Z-freelingyne (Z-11 dy = 92:8) anti E-freelingyne (E-11: ds = 98:2).

PHOSPHOGLYCERATE KINASE INHIBITORS

Disclosed are compounds of formula (I) or pharmaceutical acceptable salts thereof, wherein R1, R2, R3 and R4 are as defined in the description. Disclosed are also the methods of making said compounds, and compositions containing said compounds which are useful for inhibiting kinases such as phosphoglycerate kinase.

Reaction of C-silylated α-diazophosphines as nucleophiles toward carbonyl compounds: A mechanistic study and application to the synthesis of alkynes and α-hydroxyphosphonamides

Diversely substituted α-hydroxyphosphonamides and alkynes have been efficiently synthesized through the reaction of C-silylated α- diazophosphines with different types of aldehydes (2 equiv) in a neutral medium under very mild conditions. The reaction with some chiral aldehydes is highly diastereoselective leading to phosphonamides as single diastereomers. The novel reaction is influenced by electronic and steric effects being precluded for aromatic aldehydes containing electron-releasing substituents on the phenyl ring and for bulky aliphatic aldehydes. The mechanistic studies of these processes, which are highly exothermic, provide evidence for a nucleophilic attack of the diazophosphine to the aldehyde leading to a betaine that rapidly rearranges to a diazomethylenephosphorane, which has been detected or captured in some instances. The diazomethylenephosphorane reacts with a second molecule of aldehyde according to a Wittig-type condensation, and the rate-determining step of the whole process is believed to be the decomposition of the resultant oxaphosphetane to afford the hydroxyphosphonamide and a diazocumulene. Finally, this intermediate loses molecular nitrogen giving a transient carbene that rapidly evolves toward the alkyne.

Stereoselective synthesis of freelingyne and related γ-alkylidenebutenolides via vinylogous Mukaiyama aldol additions

Following the strategy of Scheme 1, a Mukaiyama aldol addition/anti-elimination route to stereopure γ-alkylidenebutenolides 4 was established. The addition giving 27 was only moderately diastereoselective but the products lk- and ul-27 were chromatographically separable (Scheme 4). They underwent highly selective anti-eliminations in the presence of triflic anhydride-pyridine or Burgess' reagent, furnishing the thiophene-containing butenolides Z- and E-28, respectively (Scheme 5). The Mukaiyama aldol addition leading to compound 29 was 100% lk-selective when mediated by BF3 etherate and 87 : 13 ul-selective in the presence of ZnBr2 (Scheme 6). Stephens-Castro couplings of the resulting butenolides lk- and ul-29 with 3-ethynylfuran proceeded with complete conservation of the stereochemical integrity (Scheme 7). The subsequent anti-eliminations of water were best realized by treatment with DEAD-PPh3. They provided freelingyne (Z-9) with ds = 92 : 8 and its isomer E-9 with ds = 98 : 2 (Scheme 8). Analogously, the differently substituted (trimethylsiloxy)furans 15 or 16 provided the freelingyne analogs Z-10, E-10 and Z-11 (Schemes 6-8).

Synthesis of polycylic aromatic heterocyclic compounds via thermal isomerizations of 1,8-diarylethynylnaphthalenes

The palladium catalyzed reaction between 1,8-diiodonaphthalene and ethynylarenes affords 1,8-Bis(heteroarylethynyl)naphthalenes which can cyclize thermally via diradical intermediates to the corresponding heterocyclic acenaphthene derivatives in high yiel

A SIMPLE, EFFICIENT SYNTHESIS OF 3-SUBSTITUTED FURANS

3-Substituted furan can be readily prepared in a single step via a tandem Diels-Alder/retro Diels-Alder reaction between 4-phenyloxazole and simple alkylacetylenes.