2020
DOI: 10.1021/acs.joc.0c01964
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Copper(II)-Catalyzed Domino Synthesis of 4-Benzenesulfonyl Isoxazoles from 2-Nitro-1,3-enynes, Amines, and Sodium Benzenesulfinate

Abstract: A simple and effective method for the synthesis of fully substituted 4-benzenesulfonyl isoxazoles through a copper­(II)-catalyzed three-component reaction of 2-nitro-1,3-enynes, amines, and sodium benzenesulfinate is described. The reaction proceeds smoothly under mild conditions and provides the benzenesulfonyl isoxazoles with high chemoselectivity.

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Cited by 5 publications
(4 citation statements)
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“…In addition, arylation and phosphonylation, two common functionalization reactions for the structural modifications of drug candidates, have attracted great interest in organic synthesis, synthetic methodologies, and pharmaceutical chemistry. With our continuous interests in isocyanide chemistry , and the construction of heterocycles, herein, we describe an unprecedented Mn 3+ -mediated cascade radical arylation/phosphonylation and cyclization reaction of isocyanides with aryl boronic acids/diarylphosphine oxides to afford multifunctional dibenzodiazepines (Figure , eq 2).…”
Section: Introductionmentioning
confidence: 99%
“…In addition, arylation and phosphonylation, two common functionalization reactions for the structural modifications of drug candidates, have attracted great interest in organic synthesis, synthetic methodologies, and pharmaceutical chemistry. With our continuous interests in isocyanide chemistry , and the construction of heterocycles, herein, we describe an unprecedented Mn 3+ -mediated cascade radical arylation/phosphonylation and cyclization reaction of isocyanides with aryl boronic acids/diarylphosphine oxides to afford multifunctional dibenzodiazepines (Figure , eq 2).…”
Section: Introductionmentioning
confidence: 99%
“…Among them, 1,3-enynes with a strong electron-poor nitro group at the C1 (linear) position have widely served as Michael acceptors to produce heterocyclic compounds in a combination of organo and metal catalysts (Scheme a) . In contrast, another type of nitroenyne bearing a nitro group at the C3 (branched) position, which also possessed two electrophilic sites as an ideal 3C atom synthon, gained limited attention for the preparation of diverse heterocycles . Recently, several elegant asymmetric approaches involving the domino Michael/6- exo-dig cyclization reactions of branched nitroenynes with a variety of bisnucleophiles have been successfully realized by using organocatalysts (Scheme b, left) .…”
mentioning
confidence: 99%
“…Sulfonylated heterocycles are recognized as an important class of organic molecules, having extensive applications in the field of organic chemistry, pharmaceuticals, and materials science . As such, considerable efforts have been made in the construction of the sulfonylated heterocycle framework . Among them, significant progress in the cascade difunctionalization/cyclization reaction of alkenes involving sulfonyl radical has been made, and a variety of complex sulfonylated heterocyclics have been conveniently synthesized in a step- and atom-economic way.…”
mentioning
confidence: 99%