ChemInform Abstract: From DMF to Isatin: A Novel and General One‐Pot Synthesis of Isatin and Its N‐Unsubstituted Derivatives via Nucleophilic Substitution Reactions on 1,2‐Bis(dimethylamino)‐1,2‐dichloroethene.

Abstract

on 1,2-Bis(dimethylamino)-1,2-dichloroethene. -The new route to N-unsubstituted isatins (IV) and (VI) is based on the reaction of dichloroethene with anilines (II) and (V), respectively. Isatin precursors (III) can be isolated via recrystallization. Apart from the aniline derivatives, only standard chemicals are employed as reactants. Reasonable overall yields are achieved, especially for anilines having electron-donating substituents. In order to analyze the mechanism of the reaction DFT-computations are performed. -(HUBER*, S. M.; HENNIG, A.; PUEHLHOFER, F. G.; WEISS*, R.; J. Heterocycl. Chem. 46 (2009) 3, 421-427; Inst. Org. Chem., Friedrich-Alexander-Univ., D-91054 Erlangen, Germany; Eng.) -H. Hoennerscheid 41-111