Synthesis, Stereochemistry and Ring-Chain Tautomerism of Some New Bis(1,3-perhydrooxazin-2-yl)benzene Derivatives

A.      Nan; L.      David; M.      Tintas; C.      Lar; I.      Grosu

doi:10.2174/157017811794557886

Abstract

The synthesis of some new compounds exhibiting two 1,3-perhydrooxazine units connected to the same aromatic ring and of their ditosylated derivatives was carried out in good yields by the direct condensation reaction of the corresponding aminoalcohols with aromatic dicarbonyl compounds. The stereochemistry and the ring-chain tautomerism of these compounds were investigated by NMR and EI-MS.

Keywords: 1,3-perhydrooxazine, ring-chain tautomerism, conformational analysis, like-unlike isomers, NMR, massspectrometry

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Letters in Organic Chemistry

Title: Synthesis, Stereochemistry and Ring-Chain Tautomerism of Some New Bis(1,3-perhydrooxazin-2-yl)benzene Derivatives

Volume: 8 Issue: 1

Author(s): A. Nan, L. David, M. Tintas, C. Lar and I. Grosu

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Keywords: 1,3-perhydrooxazine, ring-chain tautomerism, conformational analysis, like-unlike isomers, NMR, massspectrometry

Abstract: The synthesis of some new compounds exhibiting two 1,3-perhydrooxazine units connected to the same aromatic ring and of their ditosylated derivatives was carried out in good yields by the direct condensation reaction of the corresponding aminoalcohols with aromatic dicarbonyl compounds. The stereochemistry and the ring-chain tautomerism of these compounds were investigated by NMR and EI-MS.

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Nan A., David L., Tintas M., Lar C. and Grosu I., Synthesis, Stereochemistry and Ring-Chain Tautomerism of Some New Bis(1,3-perhydrooxazin-2-yl)benzene Derivatives, Letters in Organic Chemistry 2011; 8 (1) . https://dx.doi.org/10.2174/157017811794557886