Multicomponent Tandem Cyclization/Aromatization Reaction: Access to 2‐Substituted Naphthothiazoles and Benzothiazoles

A straightforward, metal‐free multicomponent tandem cyclization/aromatization approach for the synthesis of naphthothiazoles and benzothiazoles is described. This method employs α‐tetralones and cyclohexenones as the starting materials, styrene derivatives as a one‐carbon synthon, an ammonium salt a...

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Veröffentlicht in:European journal of organic chemistry 2024-08, Vol.27 (30), p.n/a
Hauptverfasser: Kumar, Upendra, Sharma, Ajay, Chaubey, Trayambek Nath, Pandey, Satyendra Kumar
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Sprache:eng
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Zusammenfassung:A straightforward, metal‐free multicomponent tandem cyclization/aromatization approach for the synthesis of naphthothiazoles and benzothiazoles is described. This method employs α‐tetralones and cyclohexenones as the starting materials, styrene derivatives as a one‐carbon synthon, an ammonium salt as the N source, elemental sulfur as the S source and an oxidant. This approach offers a broad substrate scope, including α‐tetralones and cyclohexenones adorned with different functional groups, resulting in moderate to high yields of the desired products. A multicomponent tandem cyclization and aromatization approach is introduced for the synthesis of naphthothiazoles and benzothiazoles from α‐tetralones and cyclohexenones, respectively. Styrene derivatives were employed to generate one‐carbon synthons through C=C bond cleavage, while an ammonium salt served as the nitrogen source and elemental sulfur served both as the sulfur source and oxidant.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400449