Recent Development on the Synthesis of Benzo[b]- and Naphtho[b]furans: A Review

Kwiecień, H.; Smist, Malgorzata; Kowalewska, Monika

doi:10.2174/157017912802651393

Cited by 55 publications

(12 citation statements)

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“…and excess Cs 2 CO 3 (2.5 equiv.) in chloroform at 70°C for 12 h led to the desired densely functionalized naphtho [1,2-b]furan product 3 a [52,53] in 73% NMR yield (60% isolated yield, entry 1). Control experiments showed the necessity of using TBAB as an additive and Cs 2 CO 3 as a base for the present transformation (entries 2-3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp³)−F Bonds

Xie

Zhang

et al. 2020

Adv Synth Catal

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The strong and unreactive CÀ F bond makes polyfluorocarbons extremely long-lived and potentially toxic. A successive selective and controllable C(sp 3)À F functionalization of polyfluoroalkylated ketones with Sand O-nucleophiles to enable efficient synthesis of pharmaceutically important fluorine-and sulfurcontaining polycyclic furan and chromene derivatives under transition metal-free conditions is demonstrated here. The combination of CÀ S/CÀ O coupling, aromatization, and cyclization cascade contribute to the accurate four/five C(sp 3)À F bond cleavage at two different sites of perfluoroalkyl chain. The formation of reactive quinoid intermediates and the necessity of using TBAB (tetrabutylammonium bromide) as additive and Cs 2 CO 3 as base were identified by detailed mechanistic studies.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp³)−F Bonds

Xie

Zhang

et al. 2020

Adv Synth Catal

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“…2-substituted benzo[b]furans/furo-pyridines are important building blocks in biologically active compounds such as anti-inflammation agents and anti-fungal activities (Scheme 1) [1][2][3][4][5][6]. Due to these excellent properties, the synthesis of these skeletons has become a hot spot in recent years [7,8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Substituted Benzo[b]furans/furo-Pyridines Catalyzed by NiCl2

2019

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The first Ni-catalyzed tandem synthesis of 2-substituted benzo[b]furans/furo-pyridines from 2-halophenols and 1-alkynes was explored under Cu-free and phosphine-free conditions. The protocol was carried out with NiCl2/5-nitro-1, 10-phenanthroline in DMA (N,N-dimethylacetamide) at 120 °C. It was found to be simple, cost effective, and have a wide substrate scope. Additionally, the method is compatible with heteroaryl substrates, resulting in the formation of 2-substituted benzo[b]furans/furo-pyridines in reasonable to good yields.

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“…Moreover, the increasing concerns of the environment demand the development of eco-friendly techniques for the preparation of nanoparticles. [36][37][38][39] Among these, synthetic naphthoĳ1,2-b]furan-3-carboxamides and benzofuran-3-carboxamides exhibit a wide range of remarkable pharmacological properties. [22][23][24] The biosynthesis of nanoparticles was carried out using green concepts, but almost all of these studies were based only on monometallic ones.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Fe, Pd, and Fe–Pd bimetallic nanoparticles and their application as recyclable catalysts for [3 + 2] cycloaddition reaction: a comparative approach

Mishra

Basavegowda

Lee

2015

Catal. Sci. Technol.

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The surface adjustment of iron nanoparticles by secondary metals increases the reaction efficiency of bimetallic nanoparticles. This paper reports a green and facile approach for the synthesis of Fe, Pd and Fe-Pd bimetallic nanoparticles using an aqueous bark extract of Ulmus davidiana and their application as magnetically recoverable catalysts for the [3 + 2] cycloaddition of 1,4-naphthoquinones or benzoquinones with β-ketoamides. The surface chemistry of the Fe-Pd bimetallic nanoparticles was determined by X-ray photoelectron spectroscopy. The morphology, size, crystallinity, weight loss, oxidation state, and ferromagnetic behavior of the synthesized nanoparticles were investigated. The bimetallic nanoparticles exhibited strong catalytic activity in high yield for the synthesis of naphthoĳ1,2-b]furan-3-carboxamides and benzofuran-3-carboxamides compared to their respective monometallic nanoparticles. The nanocatalyst was recovered easily using an external magnetic field and recycled five times without significant loss in activity.Catal. Sci. Technol. This journal is

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Recent Development on the Synthesis of Benzo[b]- and Naphtho[b]furans: A Review

Cited by 55 publications

References 0 publications

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp³)−F Bonds

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp³)−F Bonds

Synthesis of 2-Substituted Benzo[b]furans/furo-Pyridines Catalyzed by NiCl2

Biosynthesis of Fe, Pd, and Fe–Pd bimetallic nanoparticles and their application as recyclable catalysts for [3 + 2] cycloaddition reaction: a comparative approach

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Recent Development on the Synthesis of Benzo[b]- and Naphtho[b]furans: A Review

Cited by 55 publications

References 0 publications

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp3)−F Bonds

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp3)−F Bonds

Synthesis of 2-Substituted Benzo[b]furans/furo-Pyridines Catalyzed by NiCl2

Biosynthesis of Fe, Pd, and Fe–Pd bimetallic nanoparticles and their application as recyclable catalysts for [3 + 2] cycloaddition reaction: a comparative approach

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Product

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Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp³)−F Bonds

Synthesis of Polycyclic Furan and Chromene Derivatives via Cascade Reactions Enabled by Cleavage of Multiple C(sp³)−F Bonds