Rhodium(<scp>iii</scp>)-catalysed redox neutral alkylation of 3-arylbenzo[<i>d</i>]isoxazoles: easy access to substituted succinimides

Yue, Xuelin; Zhao, Xiang; Huang, Junwei; Gao, Yijie; Feng, Yadong; Cui, Xiuling

doi:10.1039/d3ob00851g

Cited by 5 publications

(2 citation statements)

References 93 publications

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“…8 In addition, they are also valuable pharmaceutical and chemical intermediates, and can be converted into pyrrolidine, pyrrolidone, lactam, and other related compounds. 9,10 Over the last several decades, many appealing methods have been developed to construct maleimides and their derivatives, including nucleophilic addition of amines to maleimides under lithium Lewis acid and amine base conditions 11 (Fig. 1a), K 2 CO 3 -mediated hydrothiolation of predecorated maleimides 12 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Electrochemically promoted thio-Michael addition of N-substituted maleimides to thiols in an aqueous medium

Wu,

Xu,

Zhou

et al. 2024

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Electrochemically promoted thio-Michael addition of N-substituted maleimides to thiols in an aqueous medium

Wu,

Xu,

Zhou

et al. 2024

Org. Biomol. Chem.

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“…The synthesis of maleimide derivatives has been extensively investigated and remains a subject of considerable research interest in recent years [4] . However, the predominant approaches focused on the alteration of monocyclic rings (Scheme 1a), [4a–e] with limited documentation on the synthesis of bicyclic maleimide frameworks [4f–h] …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Aza‐Bicyclic Maleimide Skeleton by Addition‐Ring Opening Cascade Reaction of Vinylogous Oxindole

Liao,

Zhang,

Liu

et al. 2024

Eur J Org Chem

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An efficient method has been developed to facilitate the addition‐ring opening cascade reaction of vinylogous oxindole, resulting in the synthesis of a variety of aza‐bicyclic maleimide derivatives with high yields and exceptional diastereoselectivities. Furthermore, the product could be effectively and easily transformed into the difluoromethylenecyclohexane skeleton through a dehydrofluorination process. This methodology demonstrates significant potential for the synthesis of aza‐bicyclic maleimide skeleton, which possesses biological or pharmaceutical activity.

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Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

Zhao,

Pi,

et al. 2024

Adv Synth Catal

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Herein, a Rh‐catalyzed redox C7‐spiroannulation reaction of N‐benzo[d]imidazole indolines with maleimides has been reported, chemo‐ and regio‐ selectively providing a series of N‐benzo[d]imidazole indoline fused azaspirocycles in up to 92% yield. The synthetic utility is demonstrated by the synthesis of highly functionalized nitrogen‐containing spiropolycyclic skeletons, which could be extended to maleic esters and acrylates. The products could be purified through simple filtration. The recyclable Rh catalyst and scale‐up synthesis with as low as 0.5 mol% catalyst loading makes this protocol potential application in industrial. Moreover, the efficient post‐modification of pharmaceutical molecules demonstrates its practicability.

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Rhodium(iii)-catalysed redox neutral alkylation of 3-arylbenzo[d]isoxazoles: easy access to substituted succinimides

Abstract: A convenient method for the alkylation of 3-arylbenzo[d]isoxazoles with maleimides under the redox neutral conditions has been developed, giving a series of substituted succinimides in up to 99% yield. This...

Cited by 5 publications

References 93 publications

Electrochemically promoted thio-Michael addition of N-substituted maleimides to thiols in an aqueous medium

Electrochemically promoted thio-Michael addition of N-substituted maleimides to thiols in an aqueous medium

Synthesis of Aza‐Bicyclic Maleimide Skeleton by Addition‐Ring Opening Cascade Reaction of Vinylogous Oxindole

Rhodium(III)‐Catalyzed C7‐Spiroannulation of Indolines with Maleimides: Facile Access to Aza‐Spiromulticycles

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