Dibenzo-1,5-diazocine-2,6-dione, 2-iminoindolin-3-one and N-(carbamoylmethyl)-aminobenzoic acid ester from aminobenzoic acid by multicomponent reactions
1998; Elsevier BV; Volume: 54; Issue: 39 Linguagem: Inglês
10.1016/s0040-4020(98)83046-9
ISSN1464-5416
AutoresBirgit Ebert, Ivar Ugi, M. Grosche, Eberhardt Herdtweck, Wolfgang A. Herrmann,
Tópico(s)Synthesis and biological activity
ResumoAminobenzoic acids show different types of multicomponent reactions when treated with a carbonylic component and an isocyanide in an alcoholic solution. Anthranilic acid provides dibenzo-1,5-diazocine-2,6-dione derivatives by a double Ugi four component reaction (U-4CR) or depending on the reaction conditions the U-5C-4CR product, a N-(carbamoylmethyl)anthranilic acid ester. Whereas anthranilic acid reacts hardly with ketones in that kind of multicomponent reaction. Instead the preferred reaction with isocyanides is the formation of 2-iminoindolin-3-ones. While 3-aminobenzoic acid shows no reaction, 4-aminobenzoic acid forms the U-5C-4CR product exclusively.
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