TBAF-Catalyzed <i>O</i>-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

Zhao, Yulei; Zhang, Zheng; Liu, Xu; Wang, Zongkang; Cao, Ziping; Tian, Laijin; Yue, Ming Bo; You, Jinmao

doi:10.1021/acs.joc.8b02842

Cited by 23 publications

(11 citation statements)

References 56 publications

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“…In 2019, Yulei‐Zhao and co‐workers established a novel strategy for constructing dihydroisobenzofuran derivatives 131 by selective ortho ‐nucleophilic cyclization of enaminones 130 bearing an internal alkyne in the presence of bi‐functional TBAF catalyst in THF at 35 °C (Scheme 43). [115] The advantages of the method are broad substrate scope, atom‐economic, and effectiveness for synthesizing DHIBFs under mild conditions with excellent yields.…”

Section: Resultsmentioning

confidence: 99%

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

et al. 2022

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The 2,3-dihydrobenzofuran heterocyclic systems are found in various biologically active natural and pharmaceutical products of biological relevance such as Phalarine, Rocaglamide, and Furaquinocin A. The interest in the study of 2,3-dihydrobenzofurans is constantly increasing because of their numerous biological properties such as anti-tumor, anticancer, anti-tubercular, and anti-malarial activities. Different methods have been established towards the synthesis of 2,3dihydrobenzofurans involved via intra-and inter-molecular reactions. Besides, the 1,3-dihydroisobenzofuran structure has been identified as a fundamental nucleus in many natural products, bioactive compounds, and functional molecules (e. g., Pestacin, Isopestacin, Citalopram, Xylarinol B, Matriisobenzofuran, Thunberginol F7-O-β-D-glucopyranoside). On the other hand, 1,3-disubstituted isobenzofurans are powerful structural motifs with a wide range of biological activities, like anti-inflammatory, anti-histaminic, and anti-HIV. In the last few years, a decent number of diligent synthetic approaches have been demonstrated toward synthesizing 1,3-disubstituted isobenzofurans. This review focuses on the effective synthetic routes developed to construct 2,3-dihydrobenzofurans and 1,3-dihydroisobenzofurans and their applications in recent years.

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Section: Resultsmentioning

confidence: 99%

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

et al. 2022

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“…With these optimized reaction conditions in hand, we attempted to synthesize ad iverse range of b-enaminones using the Fe-N x /CNTscatalyst due to their significance in organic synthesis. [56][57][58][59][60][61][62] As summarized in Scheme 1, the reactions between variousa romatic amines 2 and substrates 1 proceeded smoothly to afford the corresponding b-enaminones in moderate-to-good isolated yields. It is worth mentioning that these reactions were performed on the 2mmol scale.…”

Section: Resultsmentioning

confidence: 99%

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds

Ding

Huang

et al. 2020

Chemistry A European J

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C−N bond formation is regarded as a very useful and fundamental reaction for the synthesis of nitrogen‐containing molecules in both organic and pharmaceutical chemistry. Noble‐metal and homogeneous catalysts have frequently been used for C−N bond formation, however, these catalysts have a number of disadvantages, such as high cost, toxicity, and low atom economy. In this work, a low‐toxic and cheap iron complex (iron ethylene‐1,2‐diamine) has been loaded onto carbon nanotubes (CNTs) to prepare a heterogeneous single‐atom catalyst (SAC) named Fe‐Nx/CNTs. We employed this SAC in the synthesis of C−N bonds for the first time. It was found that Fe‐Nx/CNTs is an efficient catalyst for the synthesis of C−N bonds starting from aromatic amines and ketones. Its catalytic performance was excellent, giving yields of up to 96 %, six‐fold higher than the yields obtained with noble‐metal catalysts, such as AuCl3/CNTs and RhCl3/CNTs. The catalyst showed efficacy in the reactions of thirteen aromatic amine substrates, without the need for additives, and seventeen enaminones were obtained. High‐angle annular dark‐field scanning transmission electron microscopy in combination with X‐ray absorption spectroscopy revealed that the iron species were well dispersed in the Fe‐Nx/CNTs catalyst as single atoms and that Fe‐Nx might be the catalytic active species. This Fe‐Nx/CNTs catalyst has potential industrial applications as it could be cycled seven times without any significant loss of activity.

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“…[2][3][4][5][6][7] Besides, some metal-free synthetic methods of 1,3-dihydroisobenzofurans have also been disclosed. [8][9][10] On the other hand, indanones constitute the core structure of many natural products, biologically active molecules, and functional materials. [11,12] It has been proved to have a wide range of pharmacological activities, such as anti-bacterial, antiviral, anti-HIV [11a-c] and anticancer activities [11d] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

DBU/AgOTf Relay‐Catalysis Enabled One‐Pot Synthesis of 1,3‐Dihydroisobenzofurans and Its Conversion to Indanones

Wang

Huang

et al. 2022

Adv Synth Catal

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A DBU/AgOTf relay-catalyzed one-pot reaction of 2-alkynylbenzaldehydes and α-diazo esters for the efficient construction of 1,3-dihydroisobenzofuran derivatives has been documented. This protocol can tolerate a wide range of substrates and its scalability is demonstrated by the gram-scale reaction. Moreover, the obtained 1,3-dihydroisobenzofurans can be converted to indanone derivatives by a AgOTf-catalyzed ring recombination process. Both of the resulting products, 1,3-dihydroisobenzofurans and indanones, are important structural units of a variety of pharmaceuticals and natural products, and their structures are clearly confirmed by single crystal X-ray diffraction analysis.

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TBAF-Catalyzed O-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

Cited by 23 publications

References 56 publications

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

A Reusable CNT‐Supported Single‐Atom Iron Catalyst for the Highly Efficient Synthesis of C−N Bonds

DBU/AgOTf Relay‐Catalysis Enabled One‐Pot Synthesis of 1,3‐Dihydroisobenzofurans and Its Conversion to Indanones

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