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Sulfenocyclization of unsaturated ureas and thioureas

Sulfenocyclisierung ungesättigter Harnstoffe und Thioharnstoffe

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

A general method for the formation of cyclic sulfenylated 2-oxazoline, 2-thiazolines, 5,6-dihydro-4H-1,3-oxazines, and 5,6-dihydro-4H-1,3-thiazines is described. The procedure employs arylsulfenyl chloride and ethyldiisopropylamine to generate an episulfonium ion intermediate from which the cyclic products arise by internal nucleophilic displacement.

Zusammenfassung

Eine allgemeine Methode zur Herstellung cyclischer sulfenylierter 2-Oxazoline, 2-Thiazoline, 5,6-Dihydro-4H-1,3-oxazine und 5,6-Dihydro-4H-1,3-thiazine wird beschrieben. Aus Arylsulfenylchlorid und Ethyldiisopropylamin entsteht ein Episulfoniumion als Zwischenprodukt; dieses bildet durch nucleophile Umlagerung die cyclischen Produkte.

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Authors and Affiliations

  1. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Zagazig University, Zagazig, Egypt

    Z. K. Abd El-Samii

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  1. Z. K. Abd El-Samii
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Abd El-Samii, Z.K. Sulfenocyclization of unsaturated ureas and thioureas. Monatsh Chem 126, 609–614 (1995). https://doi.org/10.1007/BF00807436

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  • DOI: https://doi.org/10.1007/BF00807436

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