Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones

Abstract
A ytterbium triflate-catalyzed diastereoselective [3 + 2] cycloaddition of quinoxalinones with donor–acceptor cyclopropanes and cyclobutanes is described. A series of tetrahydropyrrolo-quinoxalinone derivatives were obtained in high yields (up to 96%) with excellent diastereoselectivities (up to 46:1). Other medicinally important heterocycles like benzoxazinone, isoquinoxalinone, and dibenzoxazepine derivatives were also suitable for the desired annulation reaction. The current method is applicable for the scale-up reaction. Further, the utility of this annulation reaction is demonstrated by the synthesis of densely functionalized proline derivatives.

Citation
Dutta, H. S., Ahmad, A., Khan, A. A., Kumar, M., Raziullah, Vaishnav, J., … Koley, D. (2021). Diastereoselective [3 + 2] Cycloaddition of Quinoxalin-2(1H)-ones with Donor–Acceptor Cyclopropanes: Efficient Synthesis of Tetrahydro pyrrolo[1,2-a]quinoxalin-4(5H)-ones. The Journal of Organic Chemistry. doi:10.1021/acs.joc.1c01872

Acknowledgements
Financial support from DST-SERB (EMR/2016/000613), CSIR-New Delhi (H.S.D., A.A., A.A.K.), and UGC-New Delhi (M.K., R.) is gratefully acknowledged. We thank the CDRI SAIF division for analytical support. CDRI communication no 10313.

Publisher
American Chemical Society (ACS)

Journal
The Journal of Organic Chemistry

DOI
10.1021/acs.joc.1c01872

Additional Links
https://pubs.acs.org/doi/10.1021/acs.joc.1c01872

Relations
Is Supplemented By:
  • [Dataset]
    Dutta, Himangsu Sekhar, Ahmad, Ashfaq, Khan, Afsar Ali, Kumar, Mohit, Raziullah, Vaishnav⧧, Jayanti, Gangwar¥, Manoj, Ampapathi⧧, Ravi Sankar, & Koley, Dipankar. (2021). CCDC 2046700: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC26PRL8. DOI: 10.5517/ccdc.csd.cc26prl8 Handle: 10754/686944
  • [Dataset]
    Dutta, Himangsu Sekhar, Ahmad, Ashfaq, Khan, Afsar Ali, Kumar, Mohit, Raziullah, Vaishnav⧧, Jayanti, Gangwar¥, Manoj, Ampapathi⧧, Ravi Sankar, & Koley, Dipankar. (2021). CCDC 2046701: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC26PRM9. DOI: 10.5517/ccdc.csd.cc26prm9 Handle: 10754/686945

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