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Communication | Regular issue | Vol 43, No. 10, 1996, pp.2091-2094
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7552
Reaction of 1,2,4-Triazine 1-Oxides with Benzyne: Formation of 1,3-Benzoxazepine and 1,3,5,6-Benzoxatriazonine Derivatives

Naoki Kakusawa, Kazunori Sakamoto, Jyoji Kurita, and Takashi Tsuchiya

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Reaction of the 6-unsubstituted 1,2,4-triazine 1-oxides (5) with benzyne gave the 1,3-benzoxazepines (8) and/or the 6-(o-hydroxyphenyl)-1,2,4-triazines (10) via the unisolable 1,3-dipolar cycloadducts (6), whereas the 6-substituted compound (12), 5,6-dimethyl-3-methoxy-1,2,4-triazine 1-oxide, afforded only the relativily stable 1,5-shift product (15) derived from the initially formed 1,3-dipolar cycloadduct (13). Heating the adduct (15) gave the novel 1,3,5,6-benzoxatriazonine derivative (16) and 2,3-dimethylbenzofuran (17).