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Metal‐Free Synthesis of Oxazolidine‐2,4‐diones and 3,3‐Disubstituted Oxindoles via ICl‐Induced Cyclization
Author(s) -
Yi Wei,
Fang XingXiao,
Liu QingYun,
Liu GongQing
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.201801250
Subject(s) - oxazolidine , chemistry , iodine monochloride , iodide , organic chemistry , amidine , chemical synthesis , iodine , combinatorial chemistry , biochemistry , in vitro
A metal‐free method for the construction of oxazolidine‐2,4‐diones and oxindoles was discussed. Using iodine monochloride (ICl) as both the reaction promoter and iodide source, the iodolactonization of N ‐Boc acrylamides proceeded readily and provided the corresponding iodo oxazolidine‐2,4‐diones and oxazolidin‐2‐ones in good isolated yields. The obtained oxazolidine‐2,4‐diones can be used as key intermediates in the synthesis of toloxatone. When N ‐alkyl‐ N ‐arylacrylamide derivatives were subjected to the same reaction, iodocarbocyclization products 3,3‐disubstituted oxindoles were obtained. The obtained oxindoles can be used as key intermediates in the synthesis of the alkaloids (±)‐esermethole and (±)‐physostigmine.