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From DMF to isatine: A novel and general one‐pot synthesis of isatine and its N‐unsubstituted derivatives via nucleophilic substitution reactions on 1,2‐bis(dimethylamino)‐1,2‐dichloro‐ethene
Author(s) -
Huber Stefan M.,
Hennig André,
Pühlhofer Frank G.,
Weiss Robert
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.8
Subject(s) - chemistry , aniline , nucleophilic substitution , nucleophile , medicinal chemistry , hydrolysis , sequence (biology) , organic chemistry , catalysis , biochemistry
3‐Imino‐2‐amino‐isatines were obtained by a one‐pot reaction of an excess of aniline (or its derivatives) with 1,2‐bis(dimethylamino)‐1,2‐dichloro‐ethene (prepared in situ from DMF). Subsequent hydrolysis yielded the corresponding isatine derivatives in reasonable to high yields. DFT calculations with regard to the mechanisms of this reaction sequence are presented. J. Heterocyclic Chem., (2009).