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Boron Trifluoride Catalyzed Divergent Synthesis of 3‐Alkenyl‐3‐amino‐2‐oxindoles and Spiro‐indeneindolones from Propargylic Alcohols
Author(s) -
Muthusamy Sengodagounder,
Balasubramani Alagesan,
Suresh Eringathodi
Publication year - 2019
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.201801106
Subject(s) - chemistry , boron trifluoride , yield (engineering) , catalysis , isatin , oxindole , one pot synthesis , boron , organic chemistry , medicinal chemistry , materials science , metallurgy
An expedient method was demonstrated for the synthesis of 3‐alkenyl‐3‐amino‐2‐oxindoles from readily available propargylic alcohols and isatin imines in the presence of BF 3 ⋅ Et 2 O as a catalyst under open‐air atmosphere. The above reaction was time‐dependent and further extended to the one‐pot synthesis of highly substituted spiro‐indeneindolones via 1,3‐amino group migration/Friedel‐Crafts cyclization. This methodology, which tolerates a broad variety of functional groups, offers versatile and atom‐economical access to 3‐alkenyl‐3‐amino‐2‐oxindole or spiro‐indeneindolone derivatives in good yield at room temperature.