Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines |
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Authors: | Maria Fridén-Saxin Tina Seifert Lars Kristian Hansen Morten Grøtli Mate Erdelyi Kristina Luthman |
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Institution: | 1. Department of Chemistry and Molecular Biology, University of Gothenburg, SE-412 96 Göteborg, Sweden;2. Department of Chemistry, University of Tromsø, NO-9037 Tromsø, Norway;3. Swedish NMR Centre, University of Gothenburg, SE-405 30 Göteborg, Sweden |
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Abstract: | Novel tricyclic N-benzylated chroman-4-one tetrahydropyrimidine derivatives have been prepared through a multi-component reaction between various 2-substituted chroman-4-one derivatives, N-methylenebenzylamine and a catalytic amount of proline under mild reaction conditions. The tricyclic structure of 1a was determined by NMR spectroscopy and confirmed by X-ray crystallography. An additional product, 2a, was isolated from the reaction mixture and its structure and conformation were determined by a combination of theoretical (Monte Carlo conformational search) and NMR-based (NOE and 3JHH couplings) conformational analysis. The NMR analysis revealed one preferred geometry for 1a and 2a in CHCl3 solution. |
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Keywords: | Multi-component reactions Cyclization Chroman-4-one Proline β-Turn |
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