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Synthesis of α‐(2‐Hydroxyphenyl)‐α‐Aminoketones by Rhodium‐Catalyzed Tandem Reaction of 1‐Sulfonyl‐1,2,3‐Triazoles and Benzoquinone‐Derived Alcohols
Author(s) -
Xu ZeFeng,
Wang Weipeng,
Cen Mengjie,
Feng Zijuan,
Duan Shengguo,
Li ChuanYing
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000487
Subject(s) - chemistry , rhodium , sulfonyl , aromatization , cascade reaction , carbene , catalysis , derivative (finance) , derivatization , claisen rearrangement , medicinal chemistry , organic chemistry , estrone , combinatorial chemistry , alkyl , biochemistry , high performance liquid chromatography , hormone , financial economics , economics
Readily available 1‐sulfonyl‐1,2,3‐triazole and benzoquinone‐derived alcohols were employed in a synthesis protocol for the formation of α‐(2‐hydroxyphenyl)‐α‐aminoketone. The cascade reaction includes the formation of rhodium carbene, O−H bond 1,3‐insertion, Claisen rearrangement as well as aromatization. Valuable benzoxazinone and 3‐aminobenzofuran were obtained after one‐step derivatization. Moreover, an estrone derivative was modified via the protocol with extraordinary efficiency.