Ruthenium(II)-Catalyzed Annulation of Oximes with Maleimides: Synthesis of Pyrrolo[3,4-<i>c</i>]isoquinoline-1,3-diones

A series of pyrroloisoquinoline-1,3-diones has been synthesized using ruthenium(II) as the catalyst and oxygen as the oxidant in a straightforward manner. The reaction proceeds through a tandem C-C/C-N bond formation process between maleimides and ketoximes, providing a direct approach for the synthesis of the titled products. This operationally simple reaction procedure supplies suitable conditions for synthesizing diverse isoquinoline-based heterocycles with a range of functional groups in moderate to good yields and compatible with gram-scale synthesis. Furthermore, the compatibility of this reaction with oxygen as a green and environmentally friendly oxidant raises the importance of the present method.

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Publication Details

Journal
Organic Letters
Published
2024-08-05
DOI
https://doi.org/10.1021/acs.orglett.4c02330
Citations
4
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.00

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article

Ruthenium(II)-Catalyzed Annulation of Oximes with Maleimides: Synthesis of Pyrrolo[3,4-c]isoquinoline-1,3-diones

Ebrahim Kianmehr, Maryam Shafiee-Pour
4 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.00
article

Ruthenium(II)-Catalyzed Annulation of Oximes with Maleimides: Synthesis of Pyrrolo[3,4-c]isoquinoline-1,3-diones

Ebrahim Kianmehr, Maryam Shafiee-Pour
article en
4 citations

Abstract

A series of pyrroloisoquinoline-1,3-diones has been synthesized using ruthenium(II) as the catalyst and oxygen as the oxidant in a straightforward manner. The reaction proceeds through a tandem C-C/C-N bond formation process between maleimides and ketoximes, providing a direct approach for the synthesis of the titled products. This operationally simple reaction procedure supplies suitable conditions for synthesizing diverse isoquinoline-based heterocycles with a range of functional groups in moderate to good yields and compatible with gram-scale synthesis. Furthermore, the compatibility of this reaction with oxygen as a green and environmentally friendly oxidant raises the importance of the present method.

Organic LettersVol. 26(33)
University of Tehran (IR)
Iran National Science Foundation, University of Tehran
Openalex Percentile: Top 28%
Catalytic C–H Functionalization Methods
1.00
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