Department of Chemistry, Jinan University, Guangzhou, 510632, China.
Mol Divers. 2021 Nov;25(4):2149-2159. doi: 10.1007/s11030-020-10109-y. Epub 2020 Jun 7.
Urease, a nickel-dependent enzyme, has a powerful catalytic activity to decompose urea into ammonia via hydrolysis reaction under mild condition. In the present work, urease was employed for the synthesis of two series of polyhydroquinoline and polyhydroacridine derivatives via one-pot condensation of the ammonia generated in situ from urea, aryl aldehydes, and dimedone or ethyl acetoacetate (i.e., Hantzsch-type reaction) in water under mild green condition. The valuable features of this enzymatic method are mild reaction conditions, short reaction times, wide substrate toleration, and high yield of products. The present work provides a novel enzymatic catalysis to synthesize polyhydroquinolines and polyhydroacridines and expands the application of urease in organic synthesis.
脲酶是一种依赖镍的酶，在温和条件下通过水解反应具有强大的催化活性，可将尿素分解为氨。在本工作中，通过在水相中温和的绿色条件下，将尿素原位产生的氨与芳醛和二亚甲基酮或乙酰乙酸乙酯（即 Hantzsch 型反应）一锅缩合，脲酶用于合成两个系列的聚氢醌和聚氢吖啶衍生物。这种酶法的优点是反应条件温和、反应时间短、底物耐受性广、产物收率高。本工作为合成聚氢醌和聚氢吖啶提供了一种新颖的酶催化方法，并扩展了脲酶在有机合成中的应用。
