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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 10
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Original Articles

Cholinergic Compounds. XIV.1: Synthesis of cis-2-methyl-5-dimethylaminomethyl-1,3-oxa thiolane methiodide

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Pages 725-732 | Published online: 05 Dec 2006

References

  • Giannella , M. , Leonelli , M. and Pigini , M. 1980 . II Farmaco, Ed. Sc. , 35 : 263
  • Elferink , J. G. R. and Salemink , C. A. 1975 . Arzneim.-Forsch. , 25 : 1702
  • Gualtieri , F. , Angeli , P. , Giannella , M. , Melchiorre , C. and Pigini , M. 1979 . Recent Advances in Receptor Chemistry , Edited by: Gualtieri , F. 267 Elsevier/North-Holland Biomedical press .
  • Triggle , D. J. and Triggle , C. R. 1976 . “ cpt 3 ” . In Chemical Pharmacology of the synapse , London : Academic Press .
  • Pigini , M. to be published
  • Rynbrandt , R. H. , Dutton , F. E. and Chidester , C. G. 1976 . J. Am. Chem. Soc. , 98 : 4882 Examples of sulfoxide amines are already known. See, for instance, and references cited therein
  • Nmr spectrum of VI, shows only one doublet for the 2-CH3 (δ 1.56) while the compound obtained according to Elferink shows two doublets in a 4:1 ratio (δ 1.56 and 1.54) (Elferink reports δ 1.48 and 1.46)
  • Under the conditions used to obtain IVa-d, pure IVa, did not show any isomerization
  • Ledaal , T. 1968 . Tetrahedron lett. , : 1683
  • Fraser , R. R. , Durst , T. , Mc Clory , M. R. , Viau , R. and Wigfield , Y. Y. 1971 . Int. J. Sulfur Chem. A , 1 : 133
  • Cockerill , A. F. , Davies , G. L. O. , Harden , R. C. and Rackham , D. M. 1973 . Chem. Rev. , 73 : 553
  • Satisfactory analytical data were obtained for all new compounds. Ir spectra were recorded with a Perkin-Elmer 257 spectrophotometer; nmr spectra were measured with a EM 390 Varian spectrometer using TMS or DSS as internal standards
  • The mixture obtained according to the procedure reported by Elferink2 melts at 159–163° (Elferink reports 169°). Nmr spectrum of the same mixture shows two doublets in a 4:1 ratio at δ 1.59 and 1.57

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