Elemental Sulfur Promoted Cyclization of <i>o</i>‐Chloronitrobenzenes and Aryl Isothiocyanates to Furnish 2‐Aminobenzothiazoles

Abstract Methods to afford 2‐aminobenzothiazoles often involve the use of o ‐aminothiophenols or aniline‐typed precursors. Herein we describe a method to furnish 2‐aminobenzothiazoles through the cyclization of o ‐chloronitrobenzenes and aryl isothiocyanates with the assistance of elemental sulfur. From the perspective of step economy, our strategy allows for the direct use of nitroarene precursors without further reduction to anilines. The scope of the reaction with respect to both substrates was investigated, and it was found that electronic properties of the aryl isothiocyanate was important for obtaining acceptable yields.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-10-23
DOI
https://doi.org/10.1002/ejoc.202401080
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Elemental Sulfur Promoted Cyclization of o‐Chloronitrobenzenes and Aryl Isothiocyanates to Furnish 2‐Aminobenzothiazoles

Tung Thanh Nguyen, Duyen K. Nguyen, Giang Binh Tran, Phong Dong Nguyen et al.
European Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

Elemental Sulfur Promoted Cyclization of o‐Chloronitrobenzenes and Aryl Isothiocyanates to Furnish 2‐Aminobenzothiazoles

Tung Thanh Nguyen, Duyen K. Nguyen, Giang Binh Tran, Phong Dong Nguyen, Khanh T. N. Ong, Thanh Hai Pham, Thi Hong Anh Nguyen, Truong K. Chau
article en

Abstract

Abstract Methods to afford 2‐aminobenzothiazoles often involve the use of o ‐aminothiophenols or aniline‐typed precursors. Herein we describe a method to furnish 2‐aminobenzothiazoles through the cyclization of o ‐chloronitrobenzenes and aryl isothiocyanates with the assistance of elemental sulfur. From the perspective of step economy, our strategy allows for the direct use of nitroarene precursors without further reduction to anilines. The scope of the reaction with respect to both substrates was investigated, and it was found that electronic properties of the aryl isothiocyanate was important for obtaining acceptable yields.

European Journal of Organic ChemistryVol. 28(3)
Vietnam National University Ho Chi Minh City (VN), Ho Chi Minh City University of Technology (VN)
Openalex Percentile: Top 86%
Sulfur-Based Synthesis Techniques
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