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The Diverse Reactivity of Homopropargylic Amines as “Masked” 1C Synthons for the Aza‐Friedel–Crafts Alkylation of Indoles
Author(s) -
Chen Hao,
Ni Min,
Bao Xiaofeng,
Wang Chan,
Liu Lingyan,
Chang Weixing,
Li Jing
Publication year - 2018
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.201701523
Subject(s) - synthon , chemistry , friedel–crafts reaction , alkylation , reagent , protonation , reactivity (psychology) , combinatorial chemistry , hydroamination , organic chemistry , catalysis , medicine , ion , alternative medicine , pathology
A novel type of “masked” 1C synthon was developed through the hydroamination cyclization‐protonation of homopropargylic amines to act as aza‐Friedel–Crafts alkylation reagents to react with indoles. A variety of 3‐(2‐pyrrolidinyl)indoles were generated in good to high yields. More significantly, some of the corresponding products display potential bioactivity against chlamydial infection, wherein they specifically target the mid‐stage of the chlamydial life cycle by interfering with RB replication.