Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine

Mookda Pattarawarapan; Sirawit Wet-osot; Dolnapa Yamano; Wong Phakhodee

doi:10.1055/s-0036-1588125

Synlett, Table of Contents

Synlett 2017; 28(05): 589-592
DOI: 10.1055/s-0036-1588125

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Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine

Mookda Pattarawarapan*

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand Email: mookdap55@gmail.com

,

Sirawit Wet-osot

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand Email: mookdap55@gmail.com

,

Dolnapa Yamano

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand Email: mookdap55@gmail.com

,

Wong Phakhodee

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand Email: mookdap55@gmail.com

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Abstract

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Abstract

A mild and convenient approach for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones under solvent-assisted grinding is reported. In the presence of 2,4,6-trichloro-1,3,5-triazine and catalytic triphenylphosphine, cyclodehydration of N-substituted anthranilic acid derivatives proceeded rapidly within minutes at room temperature. The products were also obtained in good to excellent yields by using minimal amounts of solvent and inexpensive reagents.

Key words

carboxylic acids - chemoselectivity - green chemistry - phosphorus - cyclization

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References

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