Reaction of dihydrolipoic acid with juglone and related naphthoquinones: unmasking of a spirocyclic 1,3-dithiane intermediate en route to naphtho[1,4]dithiepines |
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Authors: | Giorgia Greco Marco d'Ischia |
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Institution: | Department of Organic Chemistry and Biochemistry, University of Naples ‘Federico II’, Via Cintia 4, I-80126 Naples, Italy |
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Abstract: | The reaction of dihydrolipoic acid (DHLA) with 5-hydroxy-1,4-naphthoquinone (juglone) gives rise to the novel naphtho1,4]dithiepine derivatives through ring expansion of an unstable spirocyclic 1,3-dithiane intermediate, which was isolated and completely characterized. Reported herein is also the characterization of novel reaction products of DHLA with other naphthoquinones and the extension of the study to the spirocyclic adduct formed by reaction with a representative 2-substituted naphthoquinone. |
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Keywords: | Juglone Dihydrolipoic acid Spiro 1 3-dithiane Naphthodithiepine |
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