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Synthesis 2022; 54(24): 5451-5460
DOI: 10.1055/a-1929-2650
DOI: 10.1055/a-1929-2650
paper
One-Pot Synthesis of 2-Sulfonamidobenzo[b]thiophenes Enabled by a Mild Protonative Activation of Ynamides
H.-S.Y. acknowledges the grant (project PJ016028) from the Rural Development Administration (RDA). H.N.L. thanks Yeungnam University for financial support (2021 Yeungnam University Research Grant).
Abstract
The silica gel promoted or solvent-promoted protonative intramolecular cyclization of ynamides containing an o-(methylthio)aryl group resulted in the one-pot formation of biologically important benzo[b]thiophenes. Compared with ynamide activation methods that use strong Brønsted acids or expensive transition metals, this protocol is mild and economical. Due to these merits, various functionalized 2-amidobenzo[b]thiophenes were furnished in a convenient way.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1929-2650.
- Supporting Information
Publication History
Received: 28 June 2022
Accepted after revision: 23 August 2022
Accepted Manuscript online:
23 August 2022
Article published online:
23 September 2022
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For carbocyclizations:
For medium-sized oxacycles:
For isocoumarins:
For benzofurans:
For benzothiophenes:
For 2-amidoindoles:
For polycyclic N-heterocycles:
The related alkyne activation by silica gel and trapping by sulfur nucleophile has been reported; see:
For silica gel assisted ynamide hydrolysis, see: