Abstract
Treatment of 3-formyl-acetyl-acetone with the isomeric o-, m- and p-amino-benzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carb-oxy-phenyl-amino)-methyl-idene]pentane-2,4-dione, 1, 3-[(3-carb-oxy-phenyl-amino)-methyl-idene]pentane-2,4-dione, 2, and 3-[(4-carb-oxy-phenyl-amino)-methyl-idene]pentane-2,4-dione, 3, all C13H13NO4, that contain a planar amino-methyl-ene-pentane-2,4-dione core with a strong intra-molecular N-H⋯O hydrogen bridge. The carb-oxy-phenyl groups attached to the nitro-gen atom are almost coplanar to the central mol-ecular fragment. Depending on the position of the carboxyl unit, different supra-molecular structures with hydrogen-bonding networks are formed in the three title structures.
Highlights
Treatment of 3-formylacetylacetone with the isomeric o, m- and p-aminobenzoic acids led to the formation of the corresponding Schiff bases, namely, 3-[(2-carboxyphenylamino)methylidene]pentane-2,4-dione, 1, 3-[(3-carboxyphenylamino)methylidene]pentane-2,4-dione, 2, and 3-[(4-carboxyphenylamino)methylidene]pentane-2,4-dione, 3, all C13H13NO4, that contain a planar amino-methylene-pentane-2,4-dione core with a strong intramolecular N— HÁ Á ÁO hydrogen bridge
We were interested in the preparation of chiral N,O,O-ketiminate ligands from 3-formylacetylacetone and naturally occuring aminoacids (Hentsch et al, 2014) and recently, we reported on N,O,Pketiminates with additional PPh2 functionalities (Halz et al, 2021)
We studied the synthesis of Schiff bases derived from 3-formylacetylacetone and the isomeric o, mand p-aminobenzoic acids
Summary
The reaction of 3-formylacetylacetone with primary amines RNH2 provides easy access to enamines with an aminomethylene-pentane-2,4-dione core This approach was used for the first time as early as 1966 by Jager’s group in order to synthesize salen-type ligands from 3-formylacetylacetone and ethylenediamine (Wolf & Jager, 1966). We were interested in the preparation of chiral N,O,O-ketiminate ligands from 3-formylacetylacetone and naturally occuring aminoacids (Hentsch et al, 2014) and recently, we reported on N,O,Pketiminates with additional PPh2 functionalities (Halz et al, 2021) In this context, we studied the synthesis of Schiff bases derived from 3-formylacetylacetone and the isomeric o-, mand p-aminobenzoic acids. The corresponding crystal structures of 1, 2 and 3 are reported here
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