Friedel-Crafts Reactions of 2-Naphthol with α-Amido Sulfones and Conversion of the Products with Nucleophiles¹

Das, Biswanath; Reddy, Cheruku Ravindra; Sindhu, Chava; Sudhakar, Chithaluri; Nagendra, Siddavatam

doi:10.1055/s-0030-1258218

Cited by 9 publications

(2 citation statements)

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“…1.1 烷基化反应 1.1.1 β-萘酚的 Friedel-Crafts 烷基化反应通过 Friedel-Crafts 反应对 β-萘酚进行烷基化是实现 C-C 键构建的主要方法之一. Das 课题组 [27] 报道了 β-萘酚与 α-氨基砜发生 Friedel-Crafts 反应生成磺酰基衍生物(Scheme 1). 图式 1 β-萘酚与 α-氨基砜的 Friedel-Crafts 反应 Scheme 1 Friedel-Crafts reaction of β-naphthols with α-aminosulfones 富电子烯烃也是很好的烷化试剂, 2014 年霍聪德课题组 [28] 使用非金属的自由基阳离子 3-(4-溴苯基)-六氯锑酸铵(TBPA ＋ •SbCl 6 -)为催化剂, 实现了烯胺或烯醚与 β-萘酚新型的区域选择性 Friedel-Crafts 烷基化反应 (Scheme 2).…”

Section: β-萘酚 α 位碳-碳键的构建unclassified

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Recent Advances in the Reactions of β-Naphthol at α-Position

Liu¹,

Chen²,

Liu³

et al. 2023

Chinese Journal of Organic Chemistry

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β-Naphthol is an important synthon in organic synthesis and can participate in various chemical reactions due to its active chemical property at α-site, which has attracted a great attention from chemists. β-Naphthol can undergo various chemical transformations at α-position, such as alkylation, arylation, cyclization, amination, halogenation and so on, which can be used to construct structurally diverse naphthol derivatives with various biological activities. These naphthol derivatives can be used not only as the privileged skeletons of natural active drugs, but also as the building blocks for the preparation of the important intermediates in chemical synthesis. In recent years, chemical reactions based on β-naphthol at α-site have emerged one after another. The reactions of β-naphthol at α-position are reviewed from the aspects of C-

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Section: β-萘酚 α 位碳-碳键的构建unclassified

“…氟原子具有强电负性, 将其引入有机化合物中会改变该化合物的物理特性, 因此含氟化合物医药、新材料和农业等领域具有广泛应用 [16][17]27] . 2020 年 Hamashima 课题组 [101]…”

Section: 酚与偶氮烯的不对称unclassified

Recent Advances in the Reactions of β-Naphthol at α-Position

Liu¹,

Chen²,

Liu³

et al. 2023

Chinese Journal of Organic Chemistry

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Formation of Alkenes by Metal‐promoted Coupling Reactions

Larock

Zeni

2018

Comprehensive Organic Transformations

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Alkali Metal Reagents Grignard Reagents Boron Reagents Aluminum Reagents Indium Reagents Thallium Reagents Silicon Reagents Germanium Reagents Tin Reagents Bismuth Reagents Arsenic Reagents Sulfur Reagents Selenium Reagents Tellurium Reagents Titanium Reagents Zirconium Reagents Vanadium Reagents Molybdenum Reagents Manganese Reagents Iron Reagents Ruthenium Reagents Cobalt Reagents Nickel Reagents Palladium Reagents Copper Reagents Silver Reagents Zinc Reagents Mercury Reagents Olefin Metathesis

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Three‐Component Reactions of Aromatic Aldehydes and Two Different Nucleophiles and their Leaving Ability‐Determined Downstream Conversions of the Products

Taheri

Liu

et al. 2014

Adv Synth Catal

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Many three-component reactions of aromatic aldehydes with activated methylene derivatives and an associated nucleophile have been developed by using l-proline as the catalyst. Nucleophiles, such as indoles, thiophenols, mercaptans, 2-methylfuran and benzenesulfinic acid, could be successfully used in the reactions while the activated methylene derivatives can be 1,3-cyclohexanedione, dimedone, 1,3cyclopentanedione, 1-phenyl-3-methyl-5-pyrazolone, 4-hydroxycoumarin, 4,6-dihydroxy-2-mercaptopyrimidine, 4-hydroxy-1-methyl-2quinolone, 4-hydroxy-6-methyl-2-pyrone and 2-hydroxy-1,4-naphthoquinone. Investigation of the downstream utilization of the products from the above multicomponent reactions (MCRs) revealed that selective cleavages of carbon-carbon and carbon-heteroatom bonds in these molecules are indeed possible, which opens an avenue to access some new S N 1-type reactions. Particularly, when the MCR product of an aromatic aldehyde, dimedone and thiophenol was treated with an acid catalyst in the presence of an appropriate nucleophile, cleavage of the carbon-sulfur bond occurred preferentially, thus providing many complex molecules that cannot be attained by other known methods.

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Friedel-Crafts Reactions of 2-Naphthol with α-Amido Sulfones and Conversion of the Products with Nucleophiles¹

Cited by 9 publications

References 0 publications

Recent Advances in the Reactions of β-Naphthol at α-Position

Recent Advances in the Reactions of β-Naphthol at α-Position

Formation of Alkenes by Metal‐promoted Coupling Reactions

Three‐Component Reactions of Aromatic Aldehydes and Two Different Nucleophiles and their Leaving Ability‐Determined Downstream Conversions of the Products

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