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

✍ Scribed by Stefan M. Huber; André Hennig; Frank G. Pühlhofer; Robert Weiss

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2009
• Tongue: English
• Weight: 205 KB
• Volume: 46
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.8

✦ Synopsis

Abstract

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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).