Category: benzofurans

Kayser, Margaret M. published the artcileThe internal steric push-effect: its consequences on the reactivity of carbonyl functions in 3-substituted phthalic anhydrides, Recommanded Product: 4-Chlorophthalide, the main research area is NMR phthalic anhydride; regioselectivity nucleophilic addition; mol mechanic phthalic anhydride.

The 13C NMR for a number of 3-substituted phthalic anhydrides and corresponding lactones were measured. Substituent effects were discussed. MM2 calculations for several 3-substituted phthalic anhydrides predict that the substituent and the neighboring carbonyl group remain coplanar and within the plane of the aromatic ring. To alleviate the imposed crowding, there is an in-plane distortion of the bond angle of the substituent and the carbonyl function. The observed angle of distortion increases with increasing steric demand of the substituent, in agreement with repulsive van der Waals interaction between those two groups. Diminished reactivity of the ortho carbonyl groups vis-a-vis nucleophiles in 3-substituted phthalic anhydrides may be linked to the internal steric push-effect which causes the displacement of electrons in the CO bond from O to C.

Spectroscopy Letters published new progress about Bond angle. 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Recommanded Product: 4-Chlorophthalide.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Bohn, Irene published the artcileThe essential root oil of Pimpinella major, Synthetic Route of 13391-27-0, the main research area is Pimpinella root oil composition; sesquiterpene Pimpinella root oil.

The composition of essential oil of P. major roots from 2 different sources in Italy was analyzed and shown to contain trans-epoxypseudoisoeugenyl tiglate as the major constituent (37.34 and 19.54%) along with such minor constituents as pseudoisoeugenyl tiglate and epoxypseudoisoeugenyl 2-methylbutyrate. Other sesqui- and trinorsesquiterpenoids (C12 hydrocarbons) were present in appreciable amounts, while monoterpenoids were found only in traces. The typical oil composition enables the delimitation of this plant from several other European Pimpinella species and is a valuable tool for evaluating the com. drug Radix pimpinellae. The detection of germacrene C is significant because this is the 1st report of its occurrence in the oil of an umbelliferous plant.

Planta Medica published new progress about Aldehydes. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Synthetic Route of 13391-27-0.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ni, Yang published the artcileIron-catalyzed cross-dehydrogenative C-H amidation of benzofurans and benzothiophenes with anilines, Computed Properties of 13391-27-0, the main research area is diarylamine preparation; benzofuran aniline cross dehydrogenative amidation iron catalyst; benzothiophene aniline cross dehydrogenative amidation iron catalyst.

An efficient iron-catalyzed cross-dehydrogenative aromatic C-H amidation using DDQ as an oxidant under mild conditions was reported, providing a straightforward access to structurally diverse diarylamines 4-MeC6H4SO2NRR1 [R = 2-butylbenzofuran-3-yl, benzothiophen-3-yl, 4-MeOC6H4, etc.; R1 = 4-MeOC6H4, 3-F-4-MeOC6H3, 4-MeSC6H4, etc.] incorporating benzofuran/benzothiophene motifs. Mechanistic studies indicated that a nitrogen-centered anilino radical was involved in the C-N bond formation.

Organic Chemistry Frontiers published new progress about Amidation. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Computed Properties of 13391-27-0.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Tanemura, Kiyoshi published the artcileThe reaction of 2,3-dichloro-5,6-dicyano-p-benzoquinone with benzofurans and indoles, SDS of cas: 50551-63-8, the main research area is dichlorodicyanobenzoquinone addition benzofuran indole.

The reaction of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) with 6-methoxy-3-methylbenzofuran gave carbon-oxygen adduct I. The reaction in less polar solvents such as benzene and CH2Cl2 proceeds faster than that in more polar solvents such as THF and dioxane. In contrast, the reaction of DDQ with indoles II (R1 = H, Cl, Br, OMe, R2 = H; R1 = H, R2 = Me) gave carbon-carbon adducts III. This reaction proceeds rapidly with increasing solvent polarity.

Bulletin of the Chemical Society of Japan published new progress about dichlorodicyanobenzoquinone addition benzofuran indole. 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, SDS of cas: 50551-63-8.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Darling, Stephen D. published the artcileLithium-ammonia reduction of benzofurans, Recommanded Product: 5-Methoxy-2-methylbenzofuran, the main research area is FURAN BENZO REDN; BENZO FURAN REDN; BENZOFURANS LITHIUM AMMONIA REDN.

The reduction of 5-methoxy-2-methylbenzofuran (I), 5-methoxybenzofuran (II), 2,3- dihydro – 5 – methoxy – 2 – methylbenzofuran (III), and 2,3-dihydro-5-methoxybenzofuran (IV) with Li-NH3 systems is described. Furan ring opening was observed in the reduction of I or II when a limited amount of alc. was present in the NH3 solution With excess alc., the corresponding 5-methoxy-2,3,4,7-tetrahydrobenzofuran was formed from each substrate. A side product from the reduction of III was 2,3,4,5,6,7-hexahydro-2-methylbenzofuran (V). 21 references.

Journal of Organic Chemistry published new progress about FURAN BENZO REDN; BENZO FURAN REDN; BENZOFURANS LITHIUM AMMONIA REDN. 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Recommanded Product: 5-Methoxy-2-methylbenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Houbion, J. A. published the artcileThe synthesis of unambiguously substituted 3-hydroxyphthalides, Quality Control of 52010-22-7, the main research area is phthalide hydroxy; hydroxyphthalide; toluate bromination cyclization; formylphenyloxazoline hydrolysis cyclization; oxazolinylbenzaldehyde hydrolysis cyclization.

Hydroxyphthalides I (R = 4-, 6-, 7-Cl; 4-, 6-MeO) were obtained in 61-98% yield by photochem. bromination of II followed by hydrolysis. II (R = 4-MeO, 6-NO2) were obtained from R-2-MeC6H3CO2H by successive bromination and cyclization. I (R = 5-Cl, 5-MeO) were obtained in 63-71% yield by hydrolysis of III. III were obtained by ortho metalation-formylation of para substituted 2-aryloxazolines.

Organic Preparations and Procedures International published new progress about phthalide hydroxy; hydroxyphthalide; toluate bromination cyclization; formylphenyloxazoline hydrolysis cyclization; oxazolinylbenzaldehyde hydrolysis cyclization. 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Quality Control of 52010-22-7.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Anderson, Wayne K. published the artcileUse of 2,3-dichloropropene and 1,3-dichlorobut-2-ene as synthons for heterocyclic compounds. Synthesis of 2-methylbenzo[b]furans, 2-methylbenzo[b]thiophenes, and 4-methyl-2H-chromene, Category: benzofurans, the main research area is phenol condensation chloro alkene; thiophenol condensation chloro alkene; cyclization propene arylthio chloro; Claisen rearrangement aryloxychloropropene; benzofuran methyl; benzothiophene methyl; chromene methyl.

Addnl. data considered in indexing and abstracting are available from a source cited in the original document. The ethers I (X = O, R = H, p-Me, p-OMe, p-Cl, o-Me, o-OMe, o-Cl), prepared by condensation of the appropriate phenol with CH2:CClCH2Cl (II), underwent Claisen rearrangement to give the phenols III, acid-catalyzed cyclization of which gave 28-77% benzofurans IV (X = O). The thio ether I (X = S, R = H, p-Me, p-OMe, p-Cl, o-Me), similarly prepared from the appropriate thiophenol and II, cyclized directly on heating in PhNEt2 to give 54-80% benzothiophenes IV (X = S). Condensation of PhOH with MeCCl:CHCH2Cl gave 78% 3-chloro-1-phenoxybut-2-ene, which thermally cyclized to give 64% 4-methyl-2H-chromene.

Journal of the Chemical Society, Perkin Transactions 2: Organic and Bio-Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Category: benzofurans.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Liu, Bin published the artcileSynthesis of 1,2-phenylenedimethanols by base-promoted reduction of isobenzofuran-1(3H)-ones with silane, Computed Properties of 52010-22-7, the main research area is phenylenedimethanol preparation isobenzofuranone reduction base silane.

An efficient method for preparation of substituted 1,2-phenylenedimethanols and aliphatic 1,4-diols that are valuable intermediates in organic synthesis, was developed by the base-promoted reduction of isobenzofuran-1(3H)-ones and γ-lactones with silane under mild conditions. Compared with traditional procedures using stoichiometric amounts of metal hydrides and alkyl reductants, the present method avoids the use of sensitive reagents and is operationally simple and a broad variety of functional groups are tolerated.

Chinese Chemical Letters published new progress about Bases Role: RGT (Reagent), RACT (Reactant or Reagent). 52010-22-7 belongs to class benzofurans, name is 4-Chlorophthalide, and the molecular formula is C8H5ClO2, Computed Properties of 52010-22-7.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ueno, Atsushi published the artcileCopper-Catalyzed Formal C-H Carboxylation of Aromatic Compounds with Carbon Dioxide through Arylaluminum Intermediates, Safety of 6-Methoxybenzofuran, the main research area is aryl carboxylic acid regioselective preparation; aromatic compound alkyl amido lithium aluminate deprotonative alumination; carbon dioxide arylaluminum carboxylation copper catalyst; aromatic compounds; carbene ligands; carbon dioxide; carboxylation; copper.

The C-H bond carboxylation of various aromatic compounds with CO2 was achieved by the deprotonative alumination with a mixed alkyl amido lithium aluminate compound iBu3Al(TMP)Li followed by the NHC-copper-catalyzed carboxylation of the resulting arylaluminum species, which afforded the corresponding carboxylation products in high yield and high selectivity. In addition to benzene derivatives, heteroarenes such as benzofuran, benzothiophene, and indole derivatives are also suitable substrates. Functional groups such as Cl, Br, I, vinyl, amide, and CN could survive the reaction conditions. Some key reaction intermediates such as the copper aryl and iso-Bu complexes and their carboxylation products were isolated and structurally characterized by X-ray crystallog. analyses, thus offering important information on the reaction mechanism.

Chemistry – An Asian Journal published new progress about Alumination (deprotonative, regioselective). 50551-63-8 belongs to class benzofurans, name is 6-Methoxybenzofuran, and the molecular formula is C9H8O2, Safety of 6-Methoxybenzofuran.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Menkir, Mengistu Gemech published the artcileThe role of cesium fluoride in aryl propargyl ether Claisen rearrangement and its mechanistic elucidation: a theoretical study, Formula: C10H10O2, the main research area is cesium fluoride aryl propargyl ether Claisen rearrangement mechanistic theor.

The role of cesium fluoride (CsF) in aryl propargyl ether Claisen rearrangement and its mechanistic pathway were studied in gas and solvent phase using the d. functional theory implemented in Gaussian 09. Results indicate that the [3,3]-sigmatropic rearrangement is the rate-limiting step with ΔG‡ value of 37.1 kcal/mol in solvent phase. Also, the enolization of α-allenylketone intermediate (Int1-CsF) has a higher free energy barrier, which implies that the formation of benzopyran is not favored in the presence of CsF. However, the abstraction of the α-hydrogen atom in Int1-CsF with CsF shows a very low free energy barrier and is the most favored pathway for aryl propargyl ether Claisen rearrangement in the presence of CsF to form benzofuran. In the case of substituted aryl propargyl ethers, a methoxy group on the benzene ring lowers the activation barrier. The HOMO-LUMO, conformational and NBO anal. indicate that increasing Me substitution on the propargyl residue enhances the rearrangement reaction.

Structural Chemistry published new progress about [3,3]-Sigmatropic rearrangement (rds). 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Formula: C10H10O2.

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem