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

Himangsu Sekhar Dutta, Ashfaq Ahmad, Afsar Ali Khan, Mohit Kumar, Raziullah, Jayanti Vaishnav, Manoj Kumar Gangwar, Ravi Sankar Ampapathi, Dipankar Koley

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14 Scopus citations

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.
Original languageEnglish (US)
JournalThe Journal of Organic Chemistry
DOIs
StatePublished - Nov 15 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-11-25
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.

ASJC Scopus subject areas

  • Organic Chemistry

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