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Synlett 2017; 28(05): 589-592
DOI: 10.1055/s-0036-1588125
letter
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 14 October 2016

Accepted after revision: 27 November 2016

Publication Date:
12 December 2016 (online)

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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

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588125.
  • Supporting Information
 

  • References

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