Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines

Masahiro Teramoto; Mitsutaka Imoto; Motonori Takeda; Takumi Mizuno; Akihiro Nomoto; Akiya Ogawa

doi:10.1055/a-1430-5100

Synthesis, Table of Contents

Synthesis 2021; 53(14): 2485-2493
DOI: 10.1055/a-1430-5100

paper

Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines

Masahiro Teramoto∗

^aSeika Corporation, 1660-627 Nishihama, Wakayama 641-0036, Japan

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan

,

Mitsutaka Imoto

^aSeika Corporation, 1660-627 Nishihama, Wakayama 641-0036, Japan

,

Motonori Takeda

^aSeika Corporation, 1660-627 Nishihama, Wakayama 641-0036, Japan

,

Takumi Mizuno ∗

^aSeika Corporation, 1660-627 Nishihama, Wakayama 641-0036, Japan

,

Akihiro Nomoto

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan

,

Akiya Ogawa

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka 599-8531, Japan

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Abstract

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Abstract

This study aims to develop green and sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical and does not require any external oxidizing and/or reducing agents.

Key words

redox cyclization - benzothiazoles - 2,2′-dinitrodiphenyl disulfides - benzylamines - elemental sulfur - atom-economical

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References

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