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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 13
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Original Articles

SYNTHESIS OF NEW 3-SUBSTITUTED APORPHINES

Sándor Berényi Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen, H-4010, Hungary
,
Csaba Csutorás Department of Chemistry, Károly Eszterházy College, Eger, Leányka str. 4., H-3300, Hungary
,
Susanna Gyulai Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen, H-4010, Hungary
&
Gyula Rusznyák Department of Organic Chemistry, University of Debrecen, P.O. Box 20, Debrecen, H-4010, Hungary
Pages 1987-1992 | Received 26 May 2000, Published online: 09 Nov 2006
 
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Abstract

The methanesulfonic acid-induced rearrangement of 7-chloro-6-demethoxythebaine (10) in the presence of water or alcohols resulted in new 3-hydroxy-, or 3-alkoxy-11-hydroxy-10-methoxyaporphines (13, 14, 15, 16). O-Demethylation of the 3-methoxy derivative 14 with the methanesulfonic acid/methionine reagent-combination furnished 3,10,11-trihydroxyaporphine (18).

ACKNOWLEDGMENT

The authors thank the National Science Foundation for financial support of this work (Grants OTKA No: T029941). They also thank Dr. L. Szilágyi for recording the 1H-NMR and Dr. Z. Dinya and Dr. J. Jekö for recording the mass spectra.

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