The [4+1] cyclization reaction of 2-hydroxylimides and trimethylsulfoxonium iodide for the synthesis of 3-amino-2,3-dihydrobenzofurans

We have developed a convenient synthetic protocol for efficient construction of significant dihydrobenzofuran and benzofuran scaffolds by Lewis base-mediated annulation reaction ortho-iminophenols and ortho-vinylphenols with MBH carbonates of isatins under mild and metal-free conditions. The selective generation of different kinds of dihydrobenzofuran and benzofuran derivatives was successfully achieved by employing different substituted isatin-derived MBH carbonates with ortho-N-tosyliminophenols and ortho-vinylphenols. The features included broad substrate scopes, excellent functional group compatibility, high molecular diversity, and atomic economy.

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Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

Mushtaq,

Irfan,

Haq

et al. 2024

Front. Chem.

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2,3-Dihydrobenzofurans are noteworthy scaffolds in organic and medicinal chemistry, constituting the structural framework of many of the varied medicinally active organic compounds. Moreover, a diverse variety of biologically potent natural products also contain this heterocyclic nucleus. Reflecting on the wide biological substantiality of dihydrobenzofurans, several innovative and facile synthetic developments are evolving to achieve these heterocycles. This review summarizes the transition-metal-free, efficient, and novel synthetic pathways toward constructing the dihydrobenzofuran nucleus established after 2020.

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The [4+1] cyclization reaction of 2-hydroxylimides and trimethylsulfoxonium iodide for the synthesis of 3-amino-2,3-dihydrobenzofurans

Abstract: The [4+1] cyclization reaction of 2-hydroxylimides and the trimethylsulfoxonium iodide was investigated. This cyclization reaction exhibits wide scope and compatibility with functional groups. The 3-amino-2,3-dihydrobenzofurans were obtained in reasonable to...

Cited by 4 publications

References 28 publications

Novel synthesis of 2,3-dihydrobenzofuran-3-amines from salicylic aldehydes: Trimethylsilyl as traceless activating group

Novel synthesis of 2,3-dihydrobenzofuran-3-amines from salicylic aldehydes: Trimethylsilyl as traceless activating group

Base-Mediated Annulation of ortho-Iminophenols and ortho-Vinylphenols with MBH Carbonates of Isatins: Straightforward Access to Dihydrobenzofuran and Benzofuran Derivatives

Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

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