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Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization

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Abstract

Pyrrolo[1,2-a]indole and organosulfone are common structural motifs found in many pharmaceuticals. An efficient approach for the synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via a NaI-catalyzed sulfonyl-radical-involved cascade cyclization–isomerization process is described. By using sodium iodide as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant, various N-propargyl-substituted indoles and sulfonyl hydrazides are tolerated in this transformation, affording the corresponding products in moderate to good yields.

Graphical abstract: Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization

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Publication details

The article was received on 02 Mar 2017, accepted on 05 Apr 2017 and first published on 07 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00167C
Citation: Org. Chem. Front., 2017, Advance Article
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    Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization

    P. Zhang, Y. Gao, S. Chen, G. Tang and Y. Zhao, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00167C

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