Synlett 2022; 33(04): 386-390
DOI: 10.1055/s-0041-1737760
letter

Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization

Masahiro Teramoto
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
,
Mitsutaka Imoto
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
,
Motonori Takeda
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
,
Takumi Mizuno
a   Seika Corporation, 1660-627, Nishihama, Wakayama 641-0036, Japan
,
Akihiro Nomoto
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
,
Akiya Ogawa
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan
› Institutsangaben


Abstract

A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.

Supporting Information



Publikationsverlauf

Eingereicht: 16. November 2021

Angenommen nach Revision: 14. Dezember 2021

Artikel online veröffentlicht:
18. Januar 2022

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