Transition-Metal-Free Synthesis of 2‑Substituted Benzothiazoles from Nitrobenzenes, Methylheteroaryl Compounds, and Elemental Sulfur, Based on Nitro-Methyl Redox-Neutral Cyclization

Greener and more sustainable chemical processes are required to address increasing environmental pollution and depletion of natural resources. This paper aims to develop greener and more sustainable modern synthetic chemical processes using redox-neutral cyclization. Redox-neutral cyclization has be...

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Veröffentlicht in:Journal of organic chemistry 2020-12, Vol.85 (23), p.15213-15220
Hauptverfasser: Teramoto, Masahiro, Imoto, Mitsutaka, Takeda, Motonori, Mizuno, Takumi, Nomoto, Akihiro, Ogawa, Akiya
Format: Artikel
Sprache:eng
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Zusammenfassung:Greener and more sustainable chemical processes are required to address increasing environmental pollution and depletion of natural resources. This paper aims to develop greener and more sustainable modern synthetic chemical processes using redox-neutral cyclization. Redox-neutral cyclization has been shown to promote the efficient synthesis of 2-substituted benzothiazoles from easily available nitrobenzenes, methyl-heteroaryl compounds, and elemental sulfur in the absence of transition-metal catalysts. The 2-substituted benzothiazoles were obtained in reasonable yields through the sulfuration of electron-deficient C–H bonds with elemental sulfur. This synthetic methodology also affords a high atom economy without the use of any external oxidizing and/or reducing reagents.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02072