Dearomatization of 3-Aminophenols for Synthesis of Spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones via Hydride Transfer Strategy-Enabled [5+1] Annulations
Jia-Cheng Ge,
Yufeng Wang,
Feng-Wei Guo,
Xiangyun Kong,
Fangzhi Hu,
Shuai-Shuai Li
Affiliations
Jia-Cheng Ge
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
Yufeng Wang
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
Feng-Wei Guo
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
Xiangyun Kong
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
Fangzhi Hu
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
Shuai-Shuai Li
College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China
The Sc(OTf)3-catalyzed dearomative [5+1] annulations between readily available 3-aminophenols and O-alkyl ortho-oxybenzaldehydes were developed for synthesis of spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones. The “two-birds-with-one-stone” strategy was disclosed by the dearomatization of phenols and direct α-C(sp3)–H bond functionalization of oxygen through cascade condensation/[1,5]-hydride transfer/dearomative-cyclization process. In addition, the antifungal activity assay and derivatizations of products were conducted to further enrich the utility of the structure.