Novel glycosylidene-spiro-heterocycles from unprecedented solvent incorporation in Koenigs-Knorr-like reactions of C-(1-bromo-1-deoxy-β-D-glycopyranosyl)formamides

Chemical Communications

Volumn , Issue 7, 1999, Pages 591-592

  Somsák, László ^a   Kovács, László ^a   Gyóllai, Viktor ^a   Osz, Erzsébet ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDE DERIVATIVE; GLYCOSYLIDENE SPIRO HETEROCYCLIC DERIVATIVE; HETEROCYCLIC COMPOUND; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0345435927     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900082h     Document Type: Article

References (12)

1. L. Somsák, E. Sós, Z. Györgydeák, J.-P. Praly and G. Descotes, Tetrahedron, 1996, 52, 9121.
2. E. Osz, E. Sós, L. Somsák, L. Szilágyi and Z. Dinya, Tetrahedron, 1997, 53, 5813.
3. E. Osz, L. Somsák, L. Szilágyi, T. Docsa, B. Tóth and P. Gergely, manuscript in preparation.
4. L. Kiss and L. Somsák, Carbohydr. Res., 1996, 291, 43.
5. For a general survey on Koenigs-Knorr reactions, see: O. Lockhoff, in Methoden der Organischen Chemie (Houben-Weyl), ed. H. Hagemann and D. Klamann, Thieme, Stuttgart, 1992, vol. E14a/3, p. 782.
6. These compounds have already been isolated as syrupy by-products of the reactions of 1a,b with cyanate or thiocyanate ions in nitromethane (ref. 2, 3).
7. P. Z. Allen, Methods Carbohydr. Chem., 1962, 1, 372.
8. O. De Lucchi, U. Miotti and G. Modena, Org. React., 1991, 40, 157; D. Martin and G. Hauthal, Dimethylsulfoxid, Akademie-Verlag, Berlin, 1971, p. 302.
9. O. De Lucchi, U. Miotti and G. Modena, Org. React., 1991, 40, 157; D. Martin and G. Hauthal, Dimethylsulfoxid, Akademie-Verlag, Berlin, 1971, p. 302.
10. For Ritter-like reactions at the anomeric centre of monosaccharide derivatives, see as leading references: A. A. Pavia, S. N. Ung-Chhun and J.-L. Durand, J. Org. Chem., 1981, 46, 3158; D. Noort, G. A. van der Marel, G. J. Mulder and J. H. van Boom, Synlett, 1992, 224.
11. For Ritter-like reactions at the anomeric centre of monosaccharide derivatives, see as leading references: A. A. Pavia, S. N. Ung-Chhun and J.-L. Durand, J. Org. Chem., 1981, 46, 3158; D. Noort, G. A. van der Marel, G. J. Mulder and J. H. van Boom, Synlett, 1992, 224.
12. Our observations on the reactions of 1b with nitriles have recently been presented: V. Gyóllai and L. Somsák, 12th International Conference on Organic Synthesis, Venezia, Italy, June 28-July 2, 1998, OC-04, p. 25.