Novel stereoselective synthesis of 2,3-dihydro-1H-benzo[f]chromen-3-amine derivatives through a one-pot three-component reaction |
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Authors: | Cristina Cimarelli Davide Fratoni Gianni Palmieri |
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Affiliation: | School of Science & Technology, University of Camerino, v. S.Agostino 1, 62032 Camerino, Italy |
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Abstract: | A short and stereoselective novel synthesis of benzo[f]chromen-3-amine derivatives in good yields, through a three-component aromatic Betti type reaction under solvent free conditions is reported. The spontaneous reaction occurs in the absence of acid catalysts. The use of chiral 1-phenylethylamine or α,β-unsaturated aldehydes allowed us to prepare enantiopure benzo[f]chromen-3-amine derivatives with good stereoselectivity. Conformational analysis compared with the 1H NMR data of the products obtained, allowed us to the determine the absolute configuration, which was also confirmed by X-ray analysis. |
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