title: 2-Alkynylbenzaldoxime: a versatile building block for the generation of N-heterocycles.
abstract: 2-Alkynylbenzaldoxime as a versatile building block has been applied widely for the construction of N-heterocycles in organic synthesis. Since it could be easily transferred to isoquinoline N-oxide via intramolecular 6-endo cyclization in the presence of metal catalysts or electrophiles, the subsequent [3 + 2] cycloaddition/nucleophilic addition and rearrangement could be expected. On the other hand, a Beckmann rearrangement could occur first since an oxime moiety is present in the molecule, which would then undergo an intramolecular cyclization to furnish nitrogen-containing heterocycles. This review reports the recent advancement in the generation of N-heterocycles starting from 2-alkynylbenzaldoximes via tandem reactions based on different reaction types.
authors.affiliation: Department of Hepatology Disease, Shanghai Shuguang Hospital, Shanghai University of T.C.M., Shanghai 201203, China. gaoyueqiu@hotmail.com.
authors.forename: Linman
authors.initials: L
authors.lastname: He
authors.forename: Hongming
authors.initials: H
authors.lastname: Nie
authors.forename: Guanyinsheng
authors.initials: G
authors.lastname: Qiu
authors.forename: Yueqiu
authors.initials: Y
authors.lastname: Gao
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
mesh_terms: D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D010091:Oximes