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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*, Sirawit Wet-osot, Dolnapa Yamano, Wong Phakhodee

*Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand, Email:

M. Pattarawarapan, S. Wet-osot, D. Yamano, W. Phakhodee, Synlett, 2017, 28, 589-592.

DOI: 10.1055/s-0036-1588125 (free Supporting Information)

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Solvent-assisted grinding enables a mild and convenient synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones from N-substituted anthranilic acid derivatives in the presence of 2,4,6-trichloro-1,3,5-triazine and catalytic triphenylphosphine via a rapid cyclodehydration.

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Key Words

benzoxazinones, chemoselectivity, green chemistry, cyclization

ID: J60-Y2017