Issue 65, 2014

A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl3·7H2O in PEG-400

Abstract

The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato-1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied.

Graphical abstract: A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl3·7H2O in PEG-400

Supplementary files

Article information

Article type
Paper
Submitted
11 Jun 2014
Accepted
29 Jul 2014
First published
30 Jul 2014

RSC Adv., 2014,4, 34519-34530

Author version available

A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl3·7H2O in PEG-400

M. P. Fortes, M. M. Bassaco, T. S. Kaufman and C. C. Silveira, RSC Adv., 2014, 4, 34519 DOI: 10.1039/C4RA05625F

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