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Synthesis and crystal structures of three Schiff bases derived from 3-formyl-acetyl-acetone and benzyl-, tert-butyl- and (S)-methyl-benzyl-amine.

ABSTRACT: Treatment of 3-formyl-acetyl-acetone with the amines benzyl-amine, tert-butyl-amine and (S)-methyl-benzyl-amine led to the formation of the corresponding Schiff bases 3-[(benzyl-amino)-methyl-idene]pentane-2,4-dione, C13H15NO2 (1), 3-[(tert-butyl-amino)-methyl-idene]pentan-2,4-dione, C10H17NO2 (2) and 3-{[(S)-benz-yl(meth-yl)amino]-methyl-idene}pentane-2,4-dione, C14H17NO2 (3). The mol-ecules of all three compounds exist as enamine tautomers that contain a nearly planar amino-methyl-ene-pentane-2,4-dione core with a strong intra-molecular N-H⋯O hydrogen bridge. The R group attached to the enamine N atom has no significant influence on the bond lengths and angles of the amino-methyl-ene-pentane-2,4-dione core. The supra-molecular structures in 1-3 are mainly based on weak C-H⋯O hydrogen bonds.

SUBMITTER: Halz JH 

PROVIDER: S-EPMC10439404 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Synthesis and crystal structures of three Schiff bases derived from 3-formyl-acetyl-acetone and benzyl-, <i>tert</i>-butyl- and (<i>S</i>)-methyl-benzyl-amine.

Halz Jan Henrik JH   Hentsch Andreas A   Wagner Christoph C   Merzweiler Kurt K  

Acta crystallographica. Section E, Crystallographic communications 20230711 Pt 8

Treatment of 3-formyl-acetyl-acetone with the amines benzyl-amine, <i>tert</i>-butyl-amine and (<i>S</i>)-methyl-benzyl-amine led to the formation of the corresponding Schiff bases 3-[(benzyl-amino)-methyl-idene]pentane-2,4-dione, C<sub>13</sub>H<sub>15</sub>NO<sub>2</sub> (<b>1</b>), 3-[(<i>tert</i>-butyl-amino)-methyl-idene]pentan-2,4-dione, C<sub>10</sub>H<sub>17</sub>NO<sub>2</sub> (<b>2</b>) and 3-{[(<i>S</i>)-benz-yl(meth-yl)amino]-methyl-idene}pentane-2,4-dione, C<sub>14</sub>H<sub>17</su  ...[more]

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