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A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H, N-H - alkyne coupling

Abstract

We demonstrated a highly competitive and selective C-C and N-C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was found as the smart catalyst for 7- and 5-annulation with 1,3-migration through C-H and N-H functionalization, respectively, whereas molecular iodine performed the C-H functionalized 6-annulation with nonconvensional 1,3 H-shift. The mechanism was investigated by intermediate trapping, control, and labeling experiments.

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Publication details

The article was received on 19 Sep 2019, accepted on 28 Nov 2019 and first published on 29 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC07360D
Chem. Commun., 2019, Accepted Manuscript

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    A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H, N-H - alkyne coupling

    S. Ajarul, A. Kayet, T. K. Pati and D. K. Maiti, Chem. Commun., 2019, Accepted Manuscript , DOI: 10.1039/C9CC07360D

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