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A facile reductive ring-cleavage of isoxazole motif to synthesize 1-amino-2-acetylanthraquinone: Dual role of N,N-dimethylformamide
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Zhongkui Zhao, Renzhi Li, Yu Li
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State Key Laboratory of Fine Chemicals, Department of Catalysis Chemistry and Engineering, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, China
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Abstract |
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This work presents a facile metal-free approach for clean and highly-efficient synthesis of 1-amino-2-acetylanthraquinone via a reductive ring-cleavage of 3-methyl-anthra-[1,2-c]-isoxazol-6,11-dione by using N,N-dimethylformamide (DMF) as both catalyst and reaction media under mild reaction conditions, and 96% conversion with 95.0% selectivity of the desired product have been achieved. This finding provides a new and highly-efficient alternative to the traditional synthetic method of 1-amino-2-acetylanthraquinone by stoichiometric reduction process, and also opens a new way for the efficient reductive ring-cleavage reactions of other isoxazole motifs to corresponding ortho-amino ketones including but not limited to 1-amino-2-acetylanthraquinone.
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Keywords
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N,N-dimethylformamide; Dual roles; Reductive ring-cleavage; Isoxazole motif; ortho-amino ketones; 1-amino-2-acetylanthraquinone
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