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Simple primary amine catalyzed aerobic reductive ring-cleavage of isoxazole motif
Chinese Journal of Catalysis ( IF 15.7 ) Pub Date : 2015-02-01 , DOI: 10.1016/s1872-2067(14)60200-x
Zhongkui Zhao , Renzhi Li , Yu Li , Guiru Wang

A clean and highly efficient catalytic aerobic reductive ring-cleavage of 3–methylanthra[1,2-c]isoxazole-6,11-dione to 1-amino-2-acetylanthraquinone was performed using simple organic amines as organocatalysts and water as a green reaction medium. This method provides a new clean transformation of isoxazole-containing compounds to the corresponding ortho-amino ketones. The catalytic performance of various organic amines was carefully screened, and simple organic primary amines were found to be promising practical catalysts with outstanding catalytic performance. Isopropylamine as the organocatalyst gave 97.2% conversion of 3–methylanthra[1,2-c]isoxazole-6,11-dione, with 97.2% selectivity to 1-amino-2–acetylanthraquinone, in the presence of oxygen only, using 1 equiv. of hydrazine hydrate at room temperature for 3 h. A possible mechanism is also proposed.

中文翻译:

简单伯胺催化异恶唑基序的有氧还原环裂解

使用简单的有机胺作为有机催化剂和水作为绿色催化剂,将 3-甲基蒽[1,2-c]异恶唑-6,11-二酮清洁且高效的催化有氧还原环裂解为 1-氨基-2-乙酰蒽醌。反应介质。该方法为含异恶唑的化合物向相应的邻氨基酮提供了一种全新的清洁转化。仔细筛选了各种有机胺的催化性能,发现简单的有机伯胺是具有优异催化性能的有前途的实用催化剂。作为有机催化剂的异丙胺使 3-甲基蒽[1,2-c]异恶唑-6,11-二酮的转化率为 97.2%,对 1-氨基-2-乙酰蒽醌的选择性为 97.2%,仅在氧气存在下,使用 1 当量. 水合肼在室温下放置 3 小时。
更新日期:2015-02-01
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