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Facile synthesis of isoquinolines and isoquinoline N-oxides via a copper-catalyzed intramolecular cyclization in water† † Electronic supplementary information (ESI) available. CCDC 2095902, 2128901 and 2142641. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2ra06097c

ABSTRACT: A highly efficient method for the facile access of isoquinolines and isoquinoline N-oxides via a Cu(i)-catalyzed intramolecular cyclization of (E)-2-alkynylaryl oxime derivatives in water has been developed. This protocol was performed under simple and mild conditions without organic solvent, additives or ligands. By switching on/off a hydroxyl protecting group of oximes, the selective N–O/O–H cleavage could be triggered, delivering a series of isoquinolines and isoquinoline N-oxides, respectively, in moderate to high yields with good functional group tolerance and high atom economy. Moreover, the practicality of this method was further demonstrated by the total synthesis of moxaverine in five steps. A facile copper-catalyzed intramolecular cyclization for the selective synthesis of isoquinolines and isoquinoline N-oxides in water is described.

SUBMITTER: Zhang L

PROVIDER: S-EPMC9607880 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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