Synthesis of 1,4-thiazino- and benzo-1,4-thiazinomorphinans: their acid-catalyzed rearrangement and study of the formation of unexpected oxidation products |
| |
Authors: | Attila Sipos Levente Girán Helmut Schmidhammer |
| |
Institution: | a Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary b Institute of Pharmacy, Department of Pharmaceutical Chemistry, University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria |
| |
Abstract: | The formation of 1,4-thiazine and benzo-1,4-thiazine rings was performed at the 6,7-positions of the morphinan backbone in order to synthesize systems annulated with a new six-membered ring providing potential pharmacological activity and the opportunity of easy functionalization. An unexpected oxidation of cyclic sulfur was observed in both cases affording either sulfones or open-ringed bis-morphinan-type by-product. These phenomena are in conformity with the observations and mechanistic explanations made by several research groups in the past in connection with the photosensitized oxidation of cyclic sulfides. |
| |
Keywords: | 1 4-Thiazine Benzo-1 4-thiazine Morphinanedienes Acid-catalyzed rearrangement Oxidation |
本文献已被 ScienceDirect 等数据库收录! |
|