Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 15
83
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of 3‐Alkyl and Arylapomorphines

, , , &
Pages 2549-2558 | Received 23 Oct 2006, Published online: 09 Aug 2007

References

  • Simon , C. , Berényi , S. , Makleit , S. and Fekete , V. 1987 . Conversions of tosyl and mesyl derivatives of the morphine group, XXV: Studies of the nucleophilic substitution reactions of 6‐O‐mesyl‐7alpha‐chloro (bromo) neopine . Acta Chim. Hung. , 124 : 497 – 501 .
  • Woudenberg , R. H. and Maat , L. 1993 . Synthesis and biological activity of new etorphine analogues from 7‐chloro‐6‐demethoxythebaine and 7‐chloro‐5β‐methyl‐6‐demethoxythebaine (chemistry of opium alkaloids, part XXXVII) . Recl. Trav. Chim. Pays‐Bas. , 112 : 113 – 122 .
  • Simon , C. , Hosztafi , S. , Makleit , S. and Berényi , S. 1991 . Synthesis of C‐3 halogene substituted apocodeines and apomorphines . Synth. Commun. , 21 : 2309 – 2316 .
  • Csutorás , C. , Berényi , S. , Czakó , B. and Makleit , S. 1997 . Synthesis and transformations of novel nitrogen and sulfur containing morphinanedienes . Monatsh. Chem. , 128 : 1207 – 1273 .
  • Tóth , M. , Csutorás , C. , Gyulai , S. and Berényi , S. 2004 . Synthesis of sulfide‐ and disulfide‐type bisaporphines from thebaine . ARKIVOC , 7 : 60 – 67 .
  • Csutorás , C. , Zhang , A. , Zhang , K. , Kula , N. S. , Baldessarini , R. J. and Neumeyer , J. L. 2004 . Synthesis and neuropharmacological evaluation of R‐(‐)‐N‐alkyl‐11‐hydroxy‐noraporphines and their esters . Bioorg. Med. Chem. , 12 : 3553 – 3559 .
  • Tóth , M. , Berényi , S. , Csutorás , C. , Kula , N. S. , Zhang , K. , Baldessarini , R. J. and Neumeyer , J. L. 2006 . Synthesis and dopamine receptor binding of sulfur‐containing aporphines . Bioorg. Med. Chem. , 14 : 1918 – 1923 .
  • Zhang , A. , Csutoras , C. , Zong , R. and Neumeyer , J. L. 2005 . Synthesis of 2‐fluoro‐11‐hidroxy‐N‐propylnorapomorphine: A potential dopamine D2 agonist . Org. Lett. , 15 : 3239 – 3242 .
  • Ramsby , S. , Neumeyer , J. L. , Grigoriadis , D. and Seeman , P. 1989 . 2‐Haloaporphines as potent dopamine agonists . J. Med. Chem. , 32 : 1198 – 1201 .
  • Davies , S. G. and Pyatt , D. 1989 . Synthesis of 1‐substituted derivatives of codeine from 1‐bromocodeine via palladium catalyzed coupling reactions . Heterocycles , 28 : 163 – 167 .
  • Davies , S. G. , Goodwin , C. J. , Pyatt , D. and Smith , A. D. 2001 . Palladium catalysed elaboration of codein and morphine . J. Chem. Soc. Perkin Trans. 1. , : 1413 – 1420 .
  • Hedberg , M. H. , Jansen , M. J. , Nordvall , G. , Hjorth , S. , Unelius , L. and Johansson , A. M. 1996 . 10‐Substituted 11‐oxygenated (R)‐Aporphines: Synthesis, pharmacology, and modeling of 5‐HT1A receptor interactions . J. Med. Chem. , 39 : 3491 – 3502 .
  • Søndergaard , K. , Kristensen , J. L. , Palner , M. , Gillings , N. , Knudsen , G. M. , Roth , B. L. and Begtrup , M. 2005 . Synthesis and binding studies of 2‐arylapomorphines . Org. Biomol. Chem. , 3 : 4077 – 4081 .
  • Berényi , S. , Sipos , A. , Szabó , I. and Kálai , T. 2007 . A novel route to 2‐arylapomorphines . Synth. Commun. , 37 : 467 – 471 .
  • Csutorás , C. , Berényi , S. and Makleit , S. 1996 . A new and efficient one‐pot synthesis of apomorphine and its ring‐A halogenated derivatives . Synth. Commun. , 26 : 2251 – 2256 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.