Chemoselective [3 + 2] annulation of oxime acetate with 2-aryl-3-ethoxycarbonyl-pyrroline-4,5-dione: an entry to pyrrolo[2,3-b]pyrrole derivatives

Andhavaram Ramaraju; Atul Upare; Ewan W Blanch; Subashani Maniam; Balasubramanian Sridhar; Surendar Reddy Bathula; Chada Raji Reddy

doi:10.1039/D1OB00990G

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Chemoselective [3 + 2] annulation of oxime acetate with 2-aryl-3-ethoxycarbonyl-pyrroline-4,5-dione: an entry to pyrrolo[2,3-b]pyrrole derivatives†

Andhavaram Ramaraju,

^ab Atul Upare,^a Ewan W Blanch,^b Subashani Maniam,

^b Balasubramanian Sridhar,^c Surendar Reddy Bathula

‡^a and Chada Raji Reddy

*^a

Author affiliations

* Corresponding authors

^a Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500007, India
E-mail: rajireddy@iict.res.in

^b School of Science, STEM college, RMIT University, Melbourne, Victoria, Australia

^c Center for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

Abstract

A novel chemoselective [3 + 2] annulation reaction of easily accessible ketoxime acetate with 2-aryl-3-ethoxycarbonyl pyrroline-4,5-dione has been developed for the synthesis of unknown pyrrolo[2,3-b]pyrrole frameworks. This method involves copper-mediated N–O bond cleavage followed by the formation of carbon–carbon and carbon–nitrogen bonds. This operationally simple protocol provides broader functional group compatibility and good yields.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/D1OB00990G
Article type: Paper
Submitted: 22 May 2021
Accepted: 23 Aug 2021
First published: 23 Aug 2021

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Org. Biomol. Chem., 2021,19, 7875-7882

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Chemoselective [3 + 2] annulation of oxime acetate with 2-aryl-3-ethoxycarbonyl-pyrroline-4,5-dione: an entry to pyrrolo[2,3-b]pyrrole derivatives

A. Ramaraju, A. Upare, E. W. Blanch, S. Maniam, B. Sridhar, S. R. Bathula and C. Raji Reddy, Org. Biomol. Chem., 2021, 19, 7875 DOI: 10.1039/D1OB00990G

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Organic & Biomolecular Chemistry

Chemoselective [3 + 2] annulation of oxime acetate with 2-aryl-3-ethoxycarbonyl-pyrroline-4,5-dione: an entry to pyrrolo[2,3-b]pyrrole derivatives†

Abstract

Supplementary files

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Chemoselective [3 + 2] annulation of oxime acetate with 2-aryl-3-ethoxycarbonyl-pyrroline-4,5-dione: an entry to pyrrolo[2,3-b]pyrrole derivatives

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