232-95-1

Usage

InChI:InChI=1/C12H8O/c1-2-4-10-9(3-1)5-6-12-11(10)7-8-13-12/h1-8H

Upstream product

• 5656-67-7 acide naphtho<2,1-b>furanne carboxilique 
• 27855-91-0 (1-formyl-2-naphthyloxy)acetic acid 
• 62-53-3 aniline 
• 117516-71-9 [2]naphthyloxy-acetaldehyde diethylacetal 
• 135-19-3 β-naphthol 
• 621-62-5 chloroacetaldehyde diethyl acetal 
• 87619-46-3 1-dichloromethyl-2-methoxynaphthalene 
• 83469-37-8 2-methoxy-1-<(methoxytrimethylsilyl)methyl>naphthalene 
• 197314-86-6 Methyl 3-(2-allyloxy-1-naphthyl)propenoate 
• 174832-83-8 5-(Toluene-4-sulfonyl)-naphtho[2,1-b]furan 
• 58195-30-5 2,4a-dihydronaphtho[2,1-c][1,2]dioxine 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 88503-21-3 2-phenylmethylene-naphtho[2,1-b]furan-1(2H)-one 
• 528-46-1 phthalonic acid 
• 144-62-7 oxalic acid 
• 15719-64-9 methylammonium carbonate 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Related news

Unexpected Dual Acylation of Naphtho[2,1-b]furan at the Aryl and Hetaryl Ring: Experimental and Theoretical Study09/29/2019

Depending on the reaction conditions, the acylation of 2-ethylnaphtho[2,1-b]furan leads to the formation of a mixture of 1-acetyl-, 5-acetyl-, and 1,5-diacetyl derivatives with a widely varying ratio of components, the structure of which has been characterized by IR and NMR spectroscopy, mass sp...detailed

A naphtho[2,1-b]furan as a new fluorescent label: synthesis and spectral characterisation09/28/2019

A fluorescent naphthofuran was synthesised from an oxobenzopyran by alkaline ring contraction and coupled with various l-amino acids at their N-terminus or at side-chain functional groups, in order to evaluate its applicability as a fluorescent label for biomolecules and in peptide synthesis. Fl...detailed

Relevant academic research and scientific papers

Polycyclic heteroaromatics via hydrazine-catalyzed ring-closing carbonyl-olefin metathesis

The use of hydrazine-catalyzed ring-closing carbonyl-olefin metathesis (RCCOM) to synthesize polycyclic heteroaromatic (PHA) compounds is described. In particular, substrates bearing Lewis basic functionalities such as pyridine rings and amines, which strongly inhibit acid catalyzed RCCOM reactions, are shown to be compatible with this reaction. Using 5 mol% catalyst loadings, a variety of PHA structures can be synthesized from biaryl alkenyl aldehydes, which themselves are readily prepared by cross-coupling. This journal is

Annulation of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts: Synthesis of dihydrofuran derivatives

A new synthetic approach to dihydrofuran derivatives via the annulation reaction of β-naphthols and 4-hydroxycoumarins with vinylsulfonium salts has been developed. A variety of dihydrofuran derivatives were prepared in moderate to good yields under mild conditions. The products could be readily transformed to the corresponding furans via the dehydrogenation with DDQ.

A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes

A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)2MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional-group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.

Nickel-Catalyzed Boron Insertion into the C2-O Bond of Benzofurans

Treatment of benzofurans with bis(pinacolato)diboron and Cs2CO3 under nickel-NHC catalysis resulted in the insertion of a boron atom into the C2-O bond of benzofurans to afford the corresponding oxaborins. The scope of benzofuran substrates is wide, and the reactions proceeded without loss of functional groups such as fluoro, methoxy, and ester that are potentially reactive under nickel catalysis. The boron-inserted products proved to be useful building blocks and subsequently underwent a series of transformations, one of which led to the synthesis of fluorescent π-expanded oxaborins.

Bis(cyclopropenium)phosphines: Synthesis, Reactivity, and Applications

A straightforward route for the preparation of a set of bis(cyclopropenium)-substituted phosphines is reported. Due to their dicationic nature, these ligands depict an excellent π-acceptor character. The effect of the ligand substituent pattern on the catalytic activity of the metal complexes thereof derived is also studied. Whereas sterically demanding biaryl groups directly attached to the phosphorus atom seem to facilitate elementary steps such as the product release from the catalyst, long chain dialkylamino groups on the cyclopropenium units maximize the catalysts solubility and, thus, allow the use of typical apolar solvents such as toluene. Importantly, all new ligands prepared can be easily handled in air. Finally, the impact of the newly prepared dicationic phosphines in hydroarylation reactions is demonstrated. In particular, their use in the synthesis of several naphtho[1,2-b]furanes and naturally occurring naphthalene derivatives such as Calanquinone C is reported.

Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes

We report synthetic methodology that permits access to two oxacyclic strained intermediates, the 4,5-benzofuranyne and the 3,4-oxacyclohexyne. In situ trapping of these intermediates affords an array of heterocyclic scaffolds by the formation of one or more new C-C or C-heteroatom bonds. Experimentally determined regioselectivities were consistent with predictions made using the distortion/interaction model and were also found to be greater compared to selectivities seen in the case of trapping experiments of the corresponding N-containing intermediates. These studies demonstrate the synthetic versatility of oxacyclic arynes and alkynes for the synthesis of functionalized heterocycles, while further expanding the scope of the distortion/interaction model. Moreover, these efforts underscore the value of harnessing strained heterocyclic intermediates as a unique approach to building polycyclic heteroatom-containing frameworks.

Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers

A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is

Preparation of phenanthrenes by photocyclization of stilbenes containing a tosyl group on the central double bond. A versatile approach to the synthesis of phenanthrenes and phenanthrenoids

We have developed a useful modification of the classical preparation of phenanthrenes by UV irradiation of stilbenes in the presence of an oxidant. This modification involves the irradiation, in the presence of base, of stilbenes possessing a sulfonyl group linked to the central double bond. We have proved that this protocol can be successfully applied for the synthesis of diverse phenanthrenes and phenanthrenoids.

An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

Twelve substituted benzofurans were synthesized from their corresponding substituted 1-allyl-2-allyloxybenzenes using ruthenium-mediated C- and O-allyl isomerization followed by ring-closing metathesis.

Base-Induced Photocyclization of 1,2-Diaryl-1-tosylethenes. A Mechanistically Novel Approach to Phenanthrenes and Phenanthrenoids

(Equation presented) The irradiation with UV light of a number of 1,2-diaryl-1-tosylstilbenes, in the presence of base, leads to the corresponding phenanthrenes and heterocyclic analogues. These results are consistent with a mechanism involving the base-induced elimination of p-toluenesulfinic acid from an intermediate 9-tosyl-4a,4b-dihydrophenanthrene, formed by photochemical cyclization of the starting 1,2-diaryl-1-tosylstilbenes.