Facile, efficient and eco-friendly synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles

A concise, two-step eco-friendly approach towards the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles, is reported. The synthesis comprises the oxone-mediated thiocyanation of the starting heterocycles towards intermediate 3-thiocyanato indoles and 2-thiocyanato pyrroles, and t...

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Veröffentlicht in:	Tetrahedron letters 2014-02, Vol.55 (9), p.1648-1652
Hauptverfasser:	Kuhn, Bruna L., Fortes, Margiani P., Kaufman, Teodoro S., Silveira, Claudio C.
Format:	Artikel
Sprache:	eng
Schlagworte:	5-Sulfenyl tetrazoles Derivatives Eco-friendly functionalization of heterocycles Indoles Promotion Pyrrole and indole derivatives Pyrroles Synthesis (chemistry) Tetrahedrons Tetrazoles Thiocyanation Zinc Zinc bromide promoted reaction
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Beschreibung
Zusammenfassung:	A concise, two-step eco-friendly approach towards the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles, is reported. The synthesis comprises the oxone-mediated thiocyanation of the starting heterocycles towards intermediate 3-thiocyanato indoles and 2-thiocyanato pyrroles, and their subsequent treatment with sodium azide in 2-propanol/water under zinc bromide promotion.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2014.01.101