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NIS‐Induced Enone Difunctionalization for the Synthesis of Naphtho[2,3‐ b ]furan‐4,9‐diones
Author(s) -
Liu Yun,
Ge WenHui,
Zhu YouQuan,
Hu HuaYou,
Fan Hui,
Shi YanHui,
Wu Hui
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601291
Subject(s) - chemistry , enone , aromatization , furan , intramolecular force , michael reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
An efficient synthesis of naphtho[2,3‐ b ]furan‐4,9‐diones has been developed by N ‐iodosuccinimide (NIS)‐induced enone difunctionalization with 2‐hydroxy‐1,4‐naphthoquinones. This reaction involved sequential Michael addition, intramolecular oxidative cyclization and dehydrogenative aromatization to form new C–C and C–O bonds at the α and β positions of the enones. Various enones survived under the reaction conditions and the corresponding products were obtained in moderate‐to‐excellent yields.