2-Phenylbenzo[ b ]furans: Synthesis and promoting activity on estrogen biosynthesis

Pu, Wenchen; Yuan, Yunfei; Lu, Dan; Wang, Xin; Liu, Hanwei; Wang, Chun; Wang, Fei; Zhang, Guolin

doi:10.1016/j.bmcl.2016.10.013

Cited by 11 publications

(5 citation statements)

References 18 publications

(14 reference statements)

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“…The crude product was purified using column chromatography on silica and a hexane–ethyl acetate (1:10) mixture as eluent (for all derivatives). All of these products are known, and their structures were confirmed by comparison of their melting points with the reports. − …”

Section: Methodsmentioning

confidence: 71%

“…Yellow solid (164 mg, 60% yield), mp 194–195 °C; FT-IR ν max (KBr): 3106, 1597, 1508, 1382, 1345, 1325, 851; 1 H NMR (400 MHz, chloroform- d ) δ 8.36–8.31 (m, 2H), 8.03–7.99 (m, 2H), 7.63 (d, J = 1.8 Hz, 1H), 7.50 (d, J = 8.8 Hz, 1H), 7.34 (dd, J = 8.7, 2.1 Hz, 1H), 7.20 (d, J = 0.8 Hz, 1H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 154.6, 153.8, 147.5, 135.7, 130.0, 129.1, 126.0, 125.4, 124.4, 121.1, 112.5, 104.5; known compound …”

Section: Methodsmentioning

confidence: 99%

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Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

Ranjbari

Tavakol

2021

J. Org. Chem.

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Different benzofuran derivatives are synthesized via a catalyst-free reaction between nitroepoxides and salicylaldehydes. In the employed methodology, K2CO3 and DMF have been used at 110 °C, and the reactions were completed after 12 h in 33–84% yields. The highest yields were obtained using 3-nitrosalicylaldehyde. Finally, a plausible mechanism was proposed for the reaction, and some evidence was provided for this mechanism such as the detection of released acetate anion (using FTIR) and isolation and structure determination of the critical intermediate.

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Section: Methodsmentioning

confidence: 71%

Section: Methodsmentioning

confidence: 99%

Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

Ranjbari

Tavakol

2021

J. Org. Chem.

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“…Furans are convenient intermediates in the synthesis of drugs, such as furosemide 1 , a popular diuretic, and cefuroxime 2 , a penicillin derivative [ 1 ] ( Figure 1 ). Furan compounds are used as anticancer drugs [ 2 , 3 , 4 , 5 ] and serve as a framework for the development of new HIV inhibitors [ 6 , 7 , 8 ], antioxidant [ 9 ] and antibacterial [ 10 , 11 , 12 ] drugs, and agents for the prevention and treatment of diseases associated with estrogen deficiency [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines

2023

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We describe a method to synthesize a new class of hetarylaminomethylidene derivatives of furan-2(3H)-ones. The method uses 5-(4-chlorophenyl)furan-2(3H)-one, triethyl orthoformate, and heterocyclic amines with different ring sizes and heteroatoms under refluxing in absolute isopropyl alcohol. The obtained enamines exist in an equilibrium of E- and Z-isomers, whose configurations relative to the double exocyclic C=C bond were confirmed with a set of NMR spectroscopy data. The E-/Z-equilibrium of the synthesized compounds is affected by the configuration of the intermediate, the volume of its substituents, the site of enolate attack, the presence of intramolecular interactions of amino components, the time of the transformation, the order of mixing of the initial reagents, and the use of polar solvents in the NMR experiment. The advantages of the method are that the reaction time is short, the product yield is high, and product purification is easy.

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“…2-Arylbenzofuran derivatives in particular have attracted significant interest because of their potential as biological and pharmaceutical therapeutic agents [7]. For example, saprisartan (I) [8,9] acts as an angiotensin II receptor antagonist and renin-angiotensin system inhibitor, compound II displays potent hepatoprotective and antioxidant activities [10], compound III shows antitumor activity on a panel of human cancer cell lines [11], and compound IV has promotive activity on estrogen biosynthesis [12] (Figure 1). Li2CO3 [24,25].…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans

Kitamura¹,

Murata²,

Iwai³

et al. 2020

Molecules

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Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluorides with benzofurans under aerobic conditions in 1,2-DCE, using 5 mol% Pd (OAc)2 and 2 eq. of CuCl2 at 80 °C, produced a variety of 2-arylbenzofurans in moderate-to-high yields. The reaction is sensitive to the electronic nature of the substituents on the benzene ring of the triarylantimony difluorides: an electron-donating group showed higher reactivity than an electron-withdrawing group. Single crystal X-ray analysis of tri(p-methylphenyl) antimony difluoride revealed that the central antimony atom exhibits trigonal bipyramidal geometry.

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2-Phenylbenzo[ b ]furans: Synthesis and promoting activity on estrogen biosynthesis

Cited by 11 publications

References 18 publications

Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines

Palladium-Catalyzed C–H Arylation of Benzofurans with Triarylantimony Difluorides for the Synthesis of 2-Arylbenzofurans

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