Issue 13, 2024

Divergent synthesis of polythioindoles using elemental sulfur as the polysulfur source under metal-free conditions

Abstract

Here, we demonstrate the divergent synthesis of symmetrical or unsymmetrical tetrathiadiindoles and pentathiepino[6,7-b]indoles from indoles and elemental sulfur under metal-free conditions. These transformations probably involve a selective cyclization process of specific indole sites with polysulfur fragments which are in situ generated from elemental sulfur. This work features simple operation, metal-free nature, wide substrate scope, readily available starting materials, and feasible synthesis of valuable products. Furthermore, this method enables the direct assembly of active molecules that show anti-fungal activity and could be used as FIV inhibitors. Notably, temperature and oxidant play crucial roles in the selective synthesis of polythioindole derivatives.

Graphical abstract: Divergent synthesis of polythioindoles using elemental sulfur as the polysulfur source under metal-free conditions

Supplementary files

Article information

Article type
Research Article
Submitted
09 Apr 2024
Accepted
02 May 2024
First published
14 May 2024

Org. Chem. Front., 2024,11, 3569-3575

Divergent synthesis of polythioindoles using elemental sulfur as the polysulfur source under metal-free conditions

P. Ni, J. Tan, Y. Tan, W. Jiang and G. Deng, Org. Chem. Front., 2024, 11, 3569 DOI: 10.1039/D4QO00632A

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