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Tetrahedron Letters
Volume 44, Issue 34, 18 August 2003, Pages 6459-6462
 
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doi:10.1016/S0040-4039(03)01560-0    How to Cite or Link Using DOI (Opens New Window)
Copyright © 2003 Elsevier Ltd All rights reserved.

Synthesis of aminothiazole derived morphinans

Ao Zhanga, Sander van Vlieta and John L. NeumeyerCorresponding Author Contact Information, a, E-mail The Corresponding Author

aAlcohol and Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, MA 02478, USA

Received 30 May 2003; 
revised 19 June 2003; 
accepted 23 June 2003. 
Available online 29 July 2003.

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Abstract

Two aminothiazole derived morphinans 9 and 11 were prepared for our ongoing opioid ligands study. The synthesis was initiated from levorphanol 1, which was first triflated, and then subjected to Pd-catalyzed reduction followed by nitration. The resulting two nitrated isomers were characterized by analogy to known compounds. The formation of the aminothiazole ring occurred highly selectively to yield only one product from each of the anilines 6 and 7.

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Tetrahedron Letters
Volume 44, Issue 34, 18 August 2003, Pages 6459-6462
 
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