Copper-catalyzed three-component reaction to construct thietane ring using elemental sulfur

• Published in: Tetrahedron Vol. 166; p. 134226
• Main Authors: Patel, Dixita J., Chikhalia, Kishor H.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 17-10-2024
• Subjects: Arylsulfenylation; Aza bicyclo entities; Copper(I) iodide; Elemental sulfur; Thietane; Elemental sulfur; Thietane; Arylsulfenylation; Copper(I) iodide; Aza bicyclo entities
• ISSN: 0040-4020
• DOI: 10.1016/j.tet.2024.134226

Thietanes are vital aliphatic four-membered rings associated with various pharmaceuticals, building blocks and synthons of intermediates used in the total synthesis of natural products and biomolecules. Also, 4-thiazolidinone is a core pharmacophore of many drug molecules. Based on their various applications in medicinal chemistry and organic synthesis, an effort has been made to achieve a thietane ring on 4-thiazolidinone nucleus via quasi-benzylic acid-type intramolecular rearrangement using elemental sulfur, benzyl bromide and Cu(I). The designed methodology is environmentally benign, cheap, and easily accessible, with a broad range of substrate scopes and carried out by the employment of earth-abundant metal catalysts like copper.
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•Functionalization of 4-thiazolidinone nucleus.•Construction of aza bicyclo heterocycles having thietane nucleus.•Quasi-benzylic acid-type intramolecular rearrangement.•C–H functionalization (C–S coupling).•Environmentally benign synthetic methodology.