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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 4
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Original Articles

An Advantageous Synthesis of 5,6,7,8-Tetra-Hydrotetrazolo[1,5-a]Pyridines

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Pages 551-560 | Received 23 Jul 1998, Published online: 17 Sep 2007

References

  • Ermert , P. and Vasella , A. 1991 . Helv. Chim. Acta , 74 : 2043
  • Ermert , P. , Vasella , A. , Weber , M. , Rupitz , K. and Withers , S. G. 1993 . Carbohydr. Res. , 250 : 113
  • Brandstetter , T. W. , Davis , B. , Hyett , D. , Smith , C. , Hackett , L. , Winchester , B. G. and Fleet , G. W. J. 1995 . Tetrahedron Lett. , 36 : 7511
  • Heightman , T. D. , Ermert , P. , Klein , D. and Vasella , A. 1995 . Helv. Chim. Acta , 75 : 514
  • Butler , R. N. 1977 . Adv. Heterocyc. Chem. , 21 : 378
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  • Hoos , R. , Naughton , A. B. and Vasella , A. 1992 . Helv. Chim. Acta , 75 : 1802
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  • Shing , T. K. M. 1988 . J. Chem. Soc, Chem. Commun. , : 1221
  • Fleet , G. W. J. , Ramsden , N. G. and Witty , D. R. 1989 . Tetrahedron , 45 : 319
  • Hoos , R. , Naughton , A. B. , Thiel , W. , Vasella , A. , Weber , W. , Rupitz , K. and Withers , S. G. 1993 . Helv. Chim. Acta , 76 : 2666
  • Heightman , T. D. , Galley , C. and Vasella , A. unpublished results
  • Pipelier , M. and Vasella , A. unpublished results
  • Granier , T. and Vasella , A. unpublished results
  • Known compounds were identified on the basis of their reported physical and spectroscopic data
  • Contrary to the literature procedure the addition of Hünig's base did not improve the yield nor did it accelerate the reaction
  • Paulsen , H. 1982 . Angew. Chem., Int. Ed. Engl. , 21 : 155 Cf. the reduced reactivity of di‐ and oligosaccharide‐derived glycosyl donors
  • Glänzer , B. I. , Györgydeák , Z. , Bernet , B. and Vasella , A. 1991 . Helv. Chim. Acta , 74 : 343 The structure of the sulfonamide 17 is evidenced by the strong IR absorption at 1755 cm−1 (6, 1685 cm−1) and the 19. F‐NMR signal for a CF3 group at ‐71.4 ppm. The 'H‐NMR signals for H‐C(3) at 4.39 ppm (6, 4.00 ppm) and H‐C(6) at ca. 4.50 ppm (6, 3.55 ppm) are shifted to lower‐field; the J values J4,5 = J5,6 ≍ 2.7 Hz and the long‐range coupling (W coupling) between H‐C(4) and H‐C(6) are best rationalised by assuming a 4. H5 conformation; cf
  • Meanwell , N. A. , Hewawasam , P. , Thomas , J. A. , Wright , U. K. , Russell , J. W. , Gamberdella , M. , Goldenberg , H. J. , Seiler , S. M. and Zavoico , G. B. 1993 . J. Med. Chem. , 36 : 3251

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